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DIMETHYL SULFOXIDE (DİMETİL SÜLFOKSİT)

DIMETHYL SULFOXIDE

CAS NO:67-68-5

Molecular Formula:C2H6OS; (CH3)2SO
Molecular Weight:78.129 mol


SYNONYMS
dimethyl sulfoxide;DMSO;Methyl sulfoxide;67-68-5;Methylsulfinylmethane;Dimethylsulfoxide;Dimethyl sulphoxide;Methane, sulfinylbis-;Demsodrox;Demasorb;Demavet;Dimexide;Domoso;Dromisol;Durasorb;Infiltrina;Somipront;Syntexan;Deltan;Demeso;DMS 70;DMS 90;DMS-70;Dimethylsulfoxyde [INN-French];AI3-26477;Dimetil sulfoxido [INN-Spanish];Dimethyli sulfoxidum [INN-Latin];Methyl Sulfoxide: DMSO;DIMETHYL SULFOXIDE- D6;Rimso;Dimethylsulphinyl;Dimetilsolfossido;Sulfoxide, dimethyl;Rimso 100;Diluent;dimethysulfoxide;Decap;Diemthyl sulfoxide;dimethyl suiphoxide;dimethyl-sulphoxide;dirnethyl sulfoxide;Dimethyl sulfoxixde;methylsulfmylmethane;Dimethyl Sulfoxydum;dimethyl sulf oxide;qCbPPAD]h@;Dimethyl sulfoxide BP;2-Thiapropane2-oxide;(methanesulfinyl)methane;Dimethyl sulfoxide [USAN:USP:INN:BAN];DMSO, sterile filtered;DMSO; Methyl sulfoxide;AC1Q4GSG;Methyl sulfoxide (8CI);Rimso-50 (TN);DMSO, Dimethyl Sulfoxide;DSSTox_CID_1735;(DMSO);C2H6OS;D08HVE;EC 200-664-3;Sulfinylbis-methane (9CI);AC1L19RZ;ACMC-1BH88;DSSTox_RID_76298;H3C-SO-CH3;BIDD:PXR0182;DSSTox_GSID_21735;Dimethyl sulfoxide, >=99%;Dimethyl sulfoxide, for HPLC;KSC353A9L;DMSO, 80% aqueous solution;Methane, sulfinylbis- (9CI);Dimethyl sulfoxide (USP/INN);DIMETHYL SULFOXIDE, ACS;WLN: OS1&1;Dimethyl sulfoxide, >=99.5%;Dimethyl sulfoxide, PCR Reagent;DTXSID2021735;CTK2F3095;Dimethyl sulfoxide, ACS reagent;Methyl sulfoxide, >=99%, FG;Dimethyl sulfoxide, p.a., 99%;MolPort-002-317-295;Dimethyl sulfoxide, 99% 500g;Dimethyl sulfoxide, LR, >=99%;Pharmakon1600-01506122;KS-00000VT9;ZINC5224188;Tox21_300957;ANW-42740;BDBM50026472;MFCD00002089;NSC760436;STL264194;Dimethyl sulfoxide, AR, >=99.5%;AKOS000121107;CCG-213615;DB01093;Dimethyl sulfoxide, analytical standard;LS-1568;MCULE-2005841258;NSC-760436;RL04586;RP18373;RTR-022725;CAS-67-68-5


Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH3)2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a relatively high melting point. DMSO has the unusual property that many individuals perceive a garlic-like taste in the mouth after contact with the skin. In terms of chemical structure, the molecule has idealized Cs symmetry. It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds,[3] with a nonbonded electron pair on the approximately tetrahedral sulfur atom.


Acidity
The methyl groups of DMSO are only weakly acidic, with a pKa=35. For this reason, the basicities of many weakly basic organic compounds have been examined in this solvent.
Deprotonation of DMSO requires strong bases like lithium diisopropylamide and sodium hydride. Stabilization of the resultant carbanionis provided by the S(O)R group. The sodium derivative of DMSO formed in this way is referred to as "dimsyl sodium". It is a base, e.g., for the deprotonation of ketones to form sodium enolates, phosphonium salts to form Wittig reagents, and formamidinium salts to form diaminocarbenes. It is also a potent nucleophile.


Oxidant
In organic synthesis, DMSO is used as a mild oxidant,[6] as illustrated by the Pfitzner-Moffatt oxidation and the Swern oxidation.


Ligand
Related to its ability to dissolve many salts, DMSO is a common ligand in coordination chemistry.[8] Illustrative is the complex dichlorotetrakis(dimethyl sulfoxide)ruthenium(II) (RuCl2(dmso)4). In this complex, three DMSO ligands are bonded to ruthenium through sulfur. The fourth DMSO is bonded through oxygen. In general, the oxygen-bonded mode is more common.


APPLICATIONS
Solvent
Distillation of DMSO requires a partial vacuum to achieve a lower boiling point.
DMSO is a polar aprotic solvent and is less toxic than other members of this class, such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, and HMPA. DMSO is frequently used as a solvent for chemical reactions involving salts, most notably Finkelstein reactions and other nucleophilic substitutions. It is also extensively used as an extractant in biochemistry and cell biology.[9]Because DMSO is only weakly acidic, it tolerates relatively strong bases and as such has been extensively used in the study of carbanions. A set of non-aqueous pKa values (C-H, O-H, S-H and N-H acidities) for thousands of organic compounds have been determined in DMSO solution.
Because of its high boiling point, 189 °C (372 °F), DMSO evaporates slowly at normal atmospheric pressure. Samples dissolved in DMSO cannot be as easily recovered compared to other solvents, as it is very difficult to remove all traces of DMSO by conventional rotary evaporation. One technique to fully recover samples is removal of the organic solvent by evaporation followed by addition of water (to dissolve DMSO) and cryodesiccation to remove both DMSO and water. Reactions conducted in DMSO are often diluted with water to precipitate or phase-separate products. The relatively high freezing point of DMSO, 18.5 °C (65.3 °F), means that at, or just below, room temperature it is a solid, which can limit its utility in some chemical processes (e.g. crystallization with cooling).


PHYSICAL DESCRIPTION
DIMETHYL SULFOXIDE is a clear liquid, essentially odorless. Closed cup flash point 192°F. Vapors are heavier than air. Contact with the skin may cause stinging and burning and lead to an odor of garlic on the breath. An excellent solvent that can transport toxic solutes through the skin. High vapor concentrations may cause headache, dizziness, and sedation.


PHARMACOLOGY
Dimethyl Sulfoxide may have anti-inflammatory, antioxidant and analgesic activities. Dimethyl Sulfoxide also readily penetrates cellular membranes. The membrane-penetrating ability of dimethyl sulfoxide may enhance diffusion of other substances through the skin. For this reason, mixtures of idoxuridine and dimethyl sulfoxide have been used for topical treatment of herpes zoster in the United Kingdom.
Dimethyl Sulfoxide is a highly polar organic liquid that is used widely as a chemical solvent and a free radical scavenger. It shows a range of pharmacological activity including analgesia and anti-inflammation. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect cells and tissue during cryopreservation and has been used to treat extravasation damage caused by anthracycline-based chemotherapy.


SAFETY AND HAZARDS
Hazards Identification
GHS Hazard Statements
Aggregated GHS information provided by 561 companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Reported as not meeting GHS hazard criteria by 360 of 561 companies. For more detailed information, please visitECHA C&L website
Of the 18 notification(s) provided by 201 of 561 companies with hazard statement code(s):
H315 (91.04%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (96.02%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (54.73%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501


HEALTH HAZARDS
Slight eye irritation.
Teratogen, Flammable - 2nd degree
Fire Hazard
Special Hazards of Combustion Products: Sulfur dioxide, formaldehyde, and methyl mercaptan can form
Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 87°C explosive vapour/air mixtures may be formed.
Fire Potential
Combustible when exposed to heat or flame.
Skin, Eye, and Respiratory Irritations
Skin irritation can develop at the site where DMSO is applied topically.
Safety and Hazard Properties
LEL
2.6 % (NTP, 1992)
UEL
63 % (NTP, 1992)
63%
Flammability
Lower flammable limit: 2.6% by volume; Upper flammable limit: 42% by volume
NFPA Hazard Classification
Health: 2. 2= Materials that, on intense or continued (but not chronic) exposure, could cause temporary incapacitation or possible residual injury, including those requiring the use of respiratory protective equipment that has an independent air supply. These materials are hazardous to health, but areas may be entered freely if personnel are provided with full-face mask self-contained breathing apparatus that provides complete eye protection.
Flammability: 2. 2= This degree includes materials that must be moderately heated before ignition will occur and includes Class II and IIIA combustible liquids and solids and semi-solids that readily give off ignitible vapors. Waterspray may be used to extinguish fires in these materials because the materials can be cooled below their flash points.
Reactivity: 0. 0= This degree includes materials that are normally stable, even under fire exposure conditions, and that do not react with water. Normal fire fighting procedures may be used.


PHYSICAL DANGERS
The vapour is heavier than air and may travel along the ground; distant ignition possible.
Chemical Dangers
Decomposes on heating and on burning. This produces toxic fumes including sulfur oxides. Reacts violently with strong oxidants such as perchlorates.
Explosive Limits and Potential
Explosive limits , vol% in air: 2.6-42.0
First Aid Measures
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital.
Inhalation First Aid
Fresh air, rest.
Skin First Aid
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
Eye First Aid
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Ingestion First Aid
Do NOT induce vomiting. Refer for medical attention .
Fire Fighting Measures
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water.
Wear self contained breathing apparatus for fire fighting if necessary.
To fight fire use water, foam, alcohol foam, carbon dioxide, dry chemical.
Fire Fighting
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)
Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
Other Fire Fighting Hazards
Special hazards arising from the substance or mixture: Carbon oxides, Sulphur oxides
Accidental Release Measures
Isolation and Evacuation
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.


Spillage Disposal
Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Cleanup Methods
Accidental Release Measures. Personal precaustions, protective equipment and emergency procedure: Avoid breathing vapors, mist or gas. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let products enter drains.; Methods and materials for containment adn cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.


DISPOSAL METHODS
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company.


HANDLING AND STORAGE
Nonfire Spill Response
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)


SAFE STORAGE
Separated from strong oxidants. Cool. Keep in the dark. Keep in a well-ventilated room.
Storage Conditions
Store away from oxidizing agents, heat, and ignition sources.
Inhalation Risk
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20°C.
Effects of Short Term Exposure
The substance is irritating to the eyes and skin. Exposure to high concentrations could cause lowering of consciousness. May accelerate skin absorption of other materials. See Notes.
Effects of Long Term Exposure
Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the liver and blood. This may result in impaired functions and lesions of blood cells.
Allowable Tolerances
Residues of dimethyl sulfoxide are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: solvent or cosolvent for formulations used before crop emerges from soil or prior to formation of edible parts of food plants.
Dimethyl sulfoxide (DMSO) ... is exempted from the requirement of a tolerance when used as an inert solvent or cosolvent in formulations with the following pesticides when used in accordance with good agricultural practices in or on the following raw agricultural commodities: (a) Carbaryl (1-naphthyl methyl-carbamate) - pea, dry, seed; pea, succulent (b) O-O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) phosphorothioate - pea, dry, seed; pea, succulent.
Fire Prevention
NO open flames. Above 87°C use a closed system, ventilation and explosion-proof electrical equipment.
Exposure Prevention
PREVENT GENERATION OF MISTS! STRICT HYGIENE!
Inhalation Prevention
Use ventilation, local exhaust or breathing protection.
Skin Prevention
Protective gloves. Protective clothing.
Eye Prevention
Wear safety spectacles.
Ingestion Prevention
Do not eat, drink, or smoke during work.
Protective Equipment and Clothing
Butyl rubber gloves, safety goggles. Respiratory filter if airborne sprays or drops are present. (USCG, 1999)
Chemical-resistant gloves, Protective eyewear.


STABILITY AND REACTIVITY
Air and Water Reactions
Denser than water and miscible in water.
Reactive Group
Sulfonates, Phosphonates, and Thiophosphonates, Organic

 

DİMETİL SÜLFOKSİT
CAS NO:67-68-5

Moleküler Formül: C2H6OS; (CH3) 2SO
Moleküler Ağırlık: 78.129 mol

SYNONYMS
dimethyl sulfoxide;DMSO;Methyl sulfoxide;67-68-5;Methylsulfinylmethane;Dimethylsulfoxide;Dimethyl sulphoxide;Methane, sulfinylbis-;Demsodrox;Demasorb;Demavet;Dimexide;Domoso;Dromisol;Durasorb;Infiltrina;Somipront;Syntexan;Deltan;Demeso;DMS 70;DMS 90;DMS-70;Dimethylsulfoxyde [INN-French];AI3-26477;Dimetil sulfoxido [INN-Spanish];Dimethyli sulfoxidum [INN-Latin];Methyl Sulfoxide: DMSO;DIMETHYL SULFOXIDE- D6;Rimso;Dimethylsulphinyl;Dimetilsolfossido;Sulfoxide, dimethyl;Rimso 100;Diluent;dimethysulfoxide;Decap;Diemthyl sulfoxide;dimethyl suiphoxide;dimethyl-sulphoxide;dirnethyl sulfoxide;Dimethyl sulfoxixde;methylsulfmylmethane;Dimethyl Sulfoxydum;dimethyl sulf oxide;qCbPPAD]h@;Dimethyl sulfoxide BP;2-Thiapropane2-oxide;(methanesulfinyl)methane;Dimethyl sulfoxide [USAN:USP:INN:BAN];DMSO, sterile filtered;DMSO; Methyl sulfoxide;AC1Q4GSG;Methyl sulfoxide (8CI);Rimso-50 (TN);DMSO, Dimethyl Sulfoxide;DSSTox_CID_1735;(DMSO);C2H6OS;D08HVE;EC 200-664-3;Sulfinylbis-methane (9CI);AC1L19RZ;ACMC-1BH88;DSSTox_RID_76298;H3C-SO-CH3;BIDD:PXR0182;DSSTox_GSID_21735;Dimethyl sulfoxide, >=99%;Dimethyl sulfoxide, for HPLC;KSC353A9L;DMSO, 80% aqueous solution;Methane, sulfinylbis- (9CI);Dimethyl sulfoxide (USP/INN);DIMETHYL SULFOXIDE, ACS;WLN: OS1&1;Dimethyl sulfoxide, >=99.5%;Dimethyl sulfoxide, PCR Reagent;DTXSID2021735;CTK2F3095;Dimethyl sulfoxide, ACS reagent;Methyl sulfoxide, >=99%, FG;Dimethyl sulfoxide, p.a., 99%;MolPort-002-317-295;Dimethyl sulfoxide, 99% 500g;Dimethyl sulfoxide, LR, >=99%;Pharmakon1600-01506122;KS-00000VT9;ZINC5224188;Tox21_300957;ANW-42740;BDBM50026472;MFCD00002089;NSC760436;STL264194;Dimethyl sulfoxide, AR, >=99.5%;AKOS000121107;CCG-213615;DB01093;Dimethyl sulfoxide, analytical standard;LS-1568;MCULE-2005841258;NSC-760436;RL04586;RP18373;RTR-022725;CAS-67-68-5


Dimetil sülfoksit (DMSO), (CH3) 2S formülüne sahip bir organosülfür bileşiğidir. Bu renksiz sıvı, hem polar hem de polar olmayan bileşikleri çözen ve suyun yanı sıra çok çeşitli organik çözücüler içinde karışabilen önemli bir polar aprotik çözücüdür. Nispeten yüksek bir erime noktasına sahiptir. DMSO, bir çok kişinin cilde temas ettikten sonra ağızda sarımsak benzeri bir tat algıladığı olağandışı bir özelliğe sahiptir. [2]
Kimyasal yapı açısından, molekül Cs simetrisini idealize etmiştir. Diğer üç koordinat S (IV) bileşikleriyle tutarlı bir trigonal piramidal moleküler geometriye sahiptir, [3] yaklaşık olarak tetrahedral sülfür atomu üzerinde bağlanmamış bir elektron çifti ile.


Asidite
DMSO'nun metil grupları, sadece pKa = 35 olan, zayıf asidiktir. Bu nedenle, birçok zayıf bazik organik bileşiğin temelleri bu çözücüde incelenmiştir.
DMSO'nun çökeltilmesi lityum diizopropilamid ve sodyum hidrit gibi güçlü bazlar gerektirir. S (O) R grubu tarafından sağlanan sonuçtaki karbanyonun stabilizasyonu. Bu şekilde oluşturulan DMSO'nun sodyum türevi "dimsil sodyum" olarak adlandırılır. Örneğin, sodyum enolatlar oluşturmak için ketonların deprotonasyonu, Wittig reaktifleri oluşturmak için fosfonyum tuzları ve diaminokarbenleri oluşturmak üzere formamidinyum tuzları olmak üzere bir bazdır. Aynı zamanda güçlü bir nükleofildir.


Oksidan
Organik sentezde, DMSO, Pfitzner - Moffatt oksidasyonu ve Swern oksidasyonu ile gösterildiği gibi hafif bir oksidan olarak kullanılır.


Ligand
Pek çok tuzun çözülme yeteneği ile ilgili olarak, DMSO, koordinasyon kimyasında yaygın bir liganddır. [8] Açıklayıcı kompleks diklorotetrakis (dimetil sülfoksit) rutenyum (II) 'dir.
diklorotetrakis (dimetil sülfoksit) rutenyum (II) (RuCl2 (dmso) 4). Bu komplekste, üç DMSO ligandı kükürt yoluyla rutenyuma bağlanır. Dördüncü DMSO oksijen yoluyla bağlanır. Genel olarak, oksijen bağlı mod daha yaygındır.


UYGULAMALAR
Çözücü
DMSO'nun damıtılması, daha düşük bir kaynama noktasına ulaşmak için kısmi bir vakum gerektirir.
DMSO bir polar aprotik çözücüdür ve dimetilformamid, dimetilasetamid, N-metil-2-pirolidon ve HMPA gibi bu sınıfın diğer üyelerinden daha az toksiktir. DMSO, özellikle Finkelstein reaksiyonları ve diğer nükleofilik ikameler olmak üzere tuzları içeren kimyasal reaksiyonlar için bir çözücü olarak sıklıkla kullanılır. Ayrıca biyokimya ve hücre biyolojisinde bir ekstraktan olarak yaygın bir şekilde kullanılmaktadır. [9] DMSO'nun sadece zayıf asidik olması nedeniyle, nispeten güçlü bazları tolere eder ve bu yüzden de carbanyonların çalışmasında yaygın olarak kullanılır. DMSO çözeltisinde binlerce organik bileşik için bir dizi susuz pKa değeri (C-H, O-H, S-H ve N-H asitliği) belirlenmiştir. [10] [11]
Yüksek kaynama noktasından dolayı, 189 ° C (372 ° F), DMSO normal atmosfer basıncında yavaş yavaş buharlaşır. DMSO içinde çözülmüş numuneler, diğer çözücülere kıyasla kolayca geri kazanılabilir, çünkü geleneksel döner buharlaştırma yoluyla tüm DMSO izlerinin çıkarılması çok zordur. Numuneleri tamamen gidermek için bir teknik, organik çözücünün buharlaştırılması, ardından su (DMSO'nun çözündürülmesi) ve hem DMSO'nun hem de suyun uzaklaştırılması için cryodesiccation'ın uzaklaştırılmasıdır. DMSO'da gerçekleştirilen reaksiyonlar, çoğu zaman, çökeltme ya da faz-ayırma ürünleri için su ile seyreltilir. DMSO'nun nispeten yüksek donma noktası, 18.5 ° C (65.3 ° F), oda sıcaklığında veya hemen altında oda sıcaklığında bir katıdır, bu da bazı kimyasal işlemlerde (örneğin soğutma ile kristalizasyon) faydasını sınırlayabilir.


FİZİKSEL TANIM
DIMETHYL SULFOXIDE esasen kokusuz, berrak bir sıvıdır. Kapalı kap parlama noktası 192 ° F. Buharlar havadan ağırdır. Cilt ile temas, batma ve yanmalara neden olabilir ve nefeste sarımsak kokusuna yol açabilir. Toksik çözücüleri deriden geçirebilen mükemmel bir çözücüdür. Yüksek buhar konsantrasyonları, baş ağrısına, baş dönmesine ve sedasyona neden olabilir.
FARMAKOLOJİ
Dimetil sülfoksit, anti-enflamatuar, antioksidan ve analjezik aktiviteye sahip olabilir. Dimetil Sülfoksit ayrıca hücresel zarlara kolaylıkla nüfuz eder. Dimetil sülfoksitin membrana nüfuz etme yeteneği, diğer maddelerin deriden difüzyonunu artırabilir. Bu nedenle, Birleşik Krallık'ta herpes zoster'ın topikal tedavisi için idoxuridin ve dimetil sülfoksit karışımları kullanılmıştır.
Dimetil Sülfoksit, kimyasal çözücü ve serbest radikal süpürücü olarak yaygın olarak kullanılan oldukça polar bir organik sıvıdır. Analjezi ve anti-enflamasyon dahil olmak üzere bir dizi farmakolojik aktivite gösterir. Biyolojik membranlara nüfuz edebilme yeteneği nedeniyle, ilaçların topikal uygulaması için bir araç olarak kullanılır. Ayrıca, kriyoprezervasyon sırasında hücreleri ve dokuları korumak için kullanılır ve antrasiklin bazlı kemoterapinin neden olduğu ekstravazyon hasarını tedavi etmek için kullanılmıştır.


GÜVENLİK VE TEHLİKELER
Tehlike TANITIMI
GHS Tehlike İfadeleri
20 bildiriden 561 firmanın ECHA C & L Envanterine sağladığı toplu GHS bilgileri. Her bildirim birden çok şirketle ilişkilendirilebilir.
561 şirketin 360'ı GHS tehlike kriterlerini karşılamadığı bildirildi. Daha detaylı bilgi için lütfenECHA C & L web sitesini ziyaret ediniz.

Tehlike bildirimi koduna sahip 561 firmanın 201'i tarafından sağlanan 18 bildirim (ler):
H315 (% 91.04): Ciltte tahrişe neden olur [Uyarı Cilt aşınması / tahrişi]
H319 (% 96.02): Ciddi göz tahrişine neden olur [Uyarı Ciddi göz hasarı / göz tahrişi]
H335 (% 54.73): Solunum yolu tahrişine neden olabilir [Uyarı Spesifik hedef organ toksisitesi, tek maruz kalma; Solunum yolu tahrişi]
Bilgiler, kirliliklere, katkı maddelerine ve diğer faktörlere bağlı olarak bildirimler arasında değişebilir. Parantez içindeki yüzde değeri, tehlike kodları sağlayan firmalardan bildirilen sınıflandırma oranını gösterir. Sadece% 10'un üzerindeki yüzde değerlerine sahip tehlike kodları gösterilir.
Önlem İfadesi Kodları
P261, P264, P271, P280, P302 + P352, P304 + P340, P305 + P351 + P338, P312, P321, P332 + P313, P337 + P313, P362, P403 + P233, P405 ve P501

 

Dimetil sülfoksit kalıntıları, iyi tarım uygulamalarına uygun olarak kullanıldığında, sadece ekinlere uygulanan pestisit formülasyonlarında kullanılan inert (veya ara sıra aktif) bileşenler olarak kullanıldığında tolerans gerekliliğinden muaf tutulur. Kullanım: Ekstre edilmeden önce kullanılan formülasyonlar için çözücü veya birlikte-çözücü, topraktan veya besin bitkilerinin yenilebilir kısımlarının oluşmasından önce ortaya çıkar.
Dimetil sülfoksit (DMSO) ... aşağıdaki ham tarımsal ürünler içinde veya üzerinde iyi tarımsal uygulamalara uygun olarak kullanıldığında aşağıdaki pestisitlere sahip formülasyonlarda tesirsiz bir çözücü veya yardımcı çözücü olarak kullanıldığında tolerans gerekliliğinden muaftır: (a) Karbaril (1-naftil metil-karbamat) - bezelye, kuru, tohum; bezelye, etli (b) O-O-Dietil O- (2-izopropil-6-metil-4-pirimidinil) fosforotioat - bezelye, kuru, tohum; bezelye, etli.

Dimethylsulfoxide (DMSO)  - chemical substance with the formula - (CH3)2SO . Colorless, odorless liquid with a specific sweetish taste (insufficiently pure product has a characteristic smell of dimethyl sulfide ). An important bipolar aprotic solvent . It is widely used in various fields of chemistry , as well as as a medicine .

EC / List no.: 200-664-3

CAS no.: 67-68-5

Mol. formula: C2H6OS

 

Systematic name: dimethyl sulfoxide

Abbreviations: DMSO, DMSO

Chem. formula: C 2 H 6 OS

Physical properties

condition: liquid

Molar mass: 78.13 g / mol

Density: 1.1004 g / cm³

Dynamic viscosity: 0.001996 Pa s

Thermal properties

Temperature

 •  melting: 18.5 ° C

 •  boiling: 189 ° C

Chemical properties

 

Solubility

 • in water: unlimited

 • in ethanol:unlimited

 • in benzene: unlimited

 • in chloroform: unlimited

It was first synthesized in 1866 by the Russian chemist Alexander Zaitsev by oxidizing dimethyl sulfide with nitric acid . Over the next few decades, studies of the properties of this compound were not systematic. But it was actively used during the First World War in the hospitals of the Russian army in the treatment of injuries, fractures, wounds. Non-toxicity and non-cumulativeness in the body contributed well to this.

 

Interest in dimethyl sulfoxide in the West increased greatly after its unique dissolving ability was discovered in 1958 . In 1960, industrial production of dimethyl sulfoxide began. After that, the number of publications devoted to the study of the properties of DMSO increased dramatically.

 

Receiving 

The main method for obtaining DMSO is the oxidation of dimethyl sulfide . In industry, this process is carried out using nitric acid . DMSO is a by-product of the pulp and paper industry . The annual production of DMSO is measured in tens of thousands of tons.

 

Under laboratory conditions, potassium periodate in an organic solvent - water system can be used for mild and selective oxidation of dimethyl sulfide . However, laboratory methods for the preparation of DMSO are of no practical importance. This is due to the inconvenience of working with dimethyl sulfide, as well as the low commercial cost of the finished solvent.

 

Physical and chemical properties 

When mixed with water, noticeable heating occurs. Reacts with methyl iodide to form a sulfoxonium ion that can react with sodium hydride.

 

Application 

Application as a solvent 

DMSO is an important bipolar aprotic solvent. It is less toxic than other members of this group, such as dimethylformamide , dimethylacetamide , N-methyl-2-pyrrolidone, HMPTA. Due to its strong dissolving power, DMSO is often used as a solvent in chemical reactions involving inorganic salts, in particular in nucleophilic substitution reactions. The acidic properties of DMSO are weak, so it has become an important solvent in the chemistry of carbanions . In DMSO, the values ​​of non-aqueous pKa were measured for hundreds of organic compounds .

 

Due to its high boiling point, DMSO evaporates extremely slowly under normal atmospheric pressure. This makes it a very convenient solvent for heating reactions. At the same time, a rather high melting point limits its use in the low temperature range. After the reaction is carried out in a DMSO solution, the reaction mixtures are most often diluted with water to precipitate organic substances.

 

The deuterated form of DMSO, also known as DMSO-d6, is a convenient solvent for NMR spectroscopy due to its high dissolving power for a wide range of substances, the simplicity of its own spectrum, and its stability at high temperatures. The disadvantages of DMSO-d6 as a solvent for NMR spectroscopy are its high viscosity, which broadens the signals in the spectrum, and its high boiling point, which makes it difficult to recover the substance after analysis. Often DMSO-d6 is mixed with CDCl 3 or CD 2 Cl 2 to lower the viscosity and melting point.

 

DMSO finds more and more applications in the production of microelectronics .

 

DMSO is more effective and safer than gasoline or dichloromethane for removing paint stains .

 

Along with nitromethane, DMSO is also a tool that removes "super-glue" (hardened, but still fresh) and uncured polyurethane foam . Apparently, DMSO reacts only with external super-glue molecules, thus forming a barrier against the penetration of DMSO into the depths (This is the only way to explain the extremely long removal of super-glue, which is effective only with prolonged friction of the super-glue surface with a cloth moistened with DMSO. deeper penetration with abundant wetting with DMSO is not observed). It is recommended to work with rubber gloves (upon contact with DMSO, the skin on the fingers wrinkles as from prolonged contact with water).

 

The properties of DMSO dissolution of deposits from engine oil (sludge, varnishes, carbon deposits) in the internals of internal combustion engines when introduced into the oil and directly into the combustion chamber are noteworthy, and the flushing efficiency is such that in some cases the release of stuck piston rings and cleaning of oil drainage holes in the pistons is achieved , however, paint and varnish coatings of engine parts may dissolve, followed by the ingress of coating flakes into the oil lines.

 

Application in biology 

DMSO is used in PCR to inhibit the pairing of parental DNA molecules. Before the start of the reaction, it is added to the PCR mixture and interacts with complementary DNA regions , preventing their pairing and reducing the number of side processes  .

 

DMSO is also used as a cryoprotectant . It is added to the cell environment to prevent cell damage during freezing [4] . Approximately 10% DMSO can be used to safely cool cells and store them at liquid nitrogen temperature .

 

Application in medicine 

Main article: Dimexidum

It is used as a cryoprotectant in transplantology .

 

As a drug, purified dimethyl sulfoxide is used in the form of aqueous solutions (10-50%), as a local anti-inflammatory and analgesic agent, as well as in ointments - to increase the transdermal transfer of active substances, since it penetrates the skin and transfers other substances in a few seconds. The trade name of the drug is " Dimexid "

 

Cleaning 

In addition to the impurity of water, dimethyl sulfoxide can also contain dimethyl sulphide and sulphones . These impurities are disposed of by keeping the DMSO for 12 hours over barium oxide , sodium hydroxide , drierite, or fresh activated alumina . After that, the substance is distilled under reduced pressure (~ 2-4 mm Hg, boiling point about 50 ° C ) over granules of sodium hydroxide or barium oxide. A 4A molecular sieve is used to store the purified DMSO .

 

Security 

DMSO penetrates easily through intact skin, therefore solutions of toxic substances in DMSO can lead to poisoning when in contact with the skin (transdermal). May irritate the skin, especially with undiluted DMSO .

 

Dimethyl sulfoxide (abbreviated as DMSO) is Dimethyl sulfoxide, unitary enterprise.  500g.a highly polar and water-miscible organic liquid. It is essentially odorless and low in toxicity. Like all dipolar aprotic solvents, DMSO has a relatively high boiling point. 

    When mixed with water, noticeable heating occurs. Reacts with methyl iodide to form a sulfoxonium ion that can react with sodium hydride.

 

Synonyms: methanesulfinylmethane, methyl sulfoxide, dimethyl (oxide) sulfur, DMSO, Dimethyl sulfoxide, DMSO.

 

 

 

 Dimethyl Sulfoxide Applications

    Dimethyl sulfoxide is an excellent solvent for the preparation of active pharmaceutical ingredients and intermediates. Many specific reactions are most effective in DMSO, resulting in higher yields. The high polarity of DMSO allows it to dissolve many compounds that other solvents cannot. DMSO itself is a reagent in the class of environmentally friendly oxidation reactions.

    The powerful soluble properties of DMSO allow high asset loading, resulting in highly concentrated formulations in agrochemical formulations. DMSO is a safe and effective liquid formulation solvent for a number of active ingredients used in herbicides, insecticides, and fungicidal formulations, including propiconazole, pinoxaden, pyroxasulfone, mentaconazole, imazafar, imazamethabenzmethyl, tribupyrimphos, cyfopriluthrin, glyphophiloflophenol.

 

Dimethyl sulfoxide as a cryopreservative

 

   DMSO has the unusual ability to drastically reduce the freezing point of water while maintaining the viability of many types of cells and tissues. It is added to the cell environment to prevent cell damage during freezing. Approximately 10% DMSO can be used to safely cool cells and store them at liquid nitrogen temperature. This led to its use in cryopreservation media for stem cells obtained from human umbilical cord blood and reproductive tissue.

 

Dimethyl sulfoxide as solvent

 

     For the production and processing of polymers, DMSO is used to produce carbon fiber and some high performance polymers. Since it can dissolve Dimethyl sulfoxide substance characteristicsmany polymers, DMSO can be used to cast polymer films and fibers useful in the manufacture of purification membranes. DMSO can be used to clean up polymer residues (polyurethane / polyester) from parts manufacturing.

 

 It is less toxic than other members of this group, such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, HMPTA. Due to its strong dissolving power, DMSO is often used as a solvent in chemical reactions involving inorganic salts, in particular in nucleophilic substitution reactions. The acidic properties of DMSO are poorly expressed, so it has become an important solvent in the chemistry of carboanions. In D MSO, the values ​​of non-aqueous pKa were measured for hundreds of organic compounds

 

Due to its high boiling point, DMSO evaporates extremely slowly under normal atmospheric pressure. This makes it a very convenient solvent for heating reactions. At the same time, a rather high melting point limits its use in the low temperature range. After the reaction is carried out in a DMSO solution, the reaction mixtures are most often diluted with water to precipitate organic substances.

 

DMSO is more effective and safer than gasoline or dichloromethane for removing paint stains.

 

Along with nitromethane, DMSO is also a means of removing “super-glue” (hardened, but still fresh) and non-hardened polyurethane foam. Apparently, DMSO reacts only with external super-glue molecules, thus forming a barrier against the penetration of DMSO into the depths (This is the only way to explain the extremely long removal of the super-glue, which is effective only with prolonged friction of the super-glue surface with a cloth moistened with DMSO. deeper penetration with abundant wetting with DMSO is Cosmetic preparations with dimethyl sulfoxidenot observed).

 

 

 

Dimethyl sulfoxide in cosmetology.

 

It has unique dissolving properties, therefore it is now widely used in medicine and cosmetology. It easily and quickly (within a few seconds) penetrates through intact skin, transferring the active substances of medicinal or cosmetic products dissolved in it. Thus, it increases the effectiveness of ointments, creams, solutions - dramatically increasing the rate of penetration of active substances through the skin barrier. In addition, DMSO has anti-inflammatory and analgesic effects, and is harmful to many bacteria. DMSO in its pure form, when it gets on the skin, can cause irritation; therefore, for medicinal purposes, its aqueous solutions of various concentrations, usually from 10 to 70 percent, are most often used.

 

 

 

Dimethyl sulfoxide in crop production.

 

     The use of DMSO as a membrane penetrator creates a "sponge" effect. The plant absorbs nutrients through the leaf surface in the shortest possible time. DMSO is effective for the delivery of nutrients to the metabolic system of the plant and pulls substances in which it is dissolved through the membranes. Once in the cell, they are included in the physiological processes occurring in it, thereby increasing the activity of enzymes, activating the processes of respiration, the synthesis of proteins and carbohydrates, activating the processes of forming the area of ​​the leaf apparatus, increasing the productivity of photosynthesis. DMSO is a source of organic sulfur. The plant uses sulfur to constantly create new healthy cells and replace old ones with them. Without sulfur, the body will produce weak and dysfunctional cells. Sulfur maintains the permeability of cell membranes. DMSO ensures the entry of nutrients into the cell and the effective removal of toxins and waste products. DMSO is safe - it does not accumulate in the plant (no traces of DMSO were found in the plants after foliar dressing).Dimexide is actively used in the fields as a part of fertilizers

 

Application phases

 

- in autumn 2 ... 3 weeks before the onset of frost:

 

winter wheat, triticale, rye, winter barley - in the tillering phase;

winter rape - in the phase of 4 ... 6 true leaves;

- in spring:

 

winter and spring wheat, triticale, rye, barley - in the tillering phase;

corn - in the phase of 5 ... 7 leaves;

sunflower - in the phase of 6 ... 8 leaves;

rapeseed - in the phase of 6 ... 8 true leaves.

    Doses for foliar dressing are from 0.006 kg to 0.04 per 1 liter of solution. (concentration depends on water quality) Costs per hectare from 149 rubles Correct and timely use of the tank mixture guarantees an increase in frost and drought resistance of plants by 25% -30%. Retains a prolonged action for the entire growing season. The use of DMSO makes it possible to reduce the dosage and save the funds of the enterprise of plant protection products to 1/2 of the minimum recommended by the manufacturer of plant nutrients by 30%.

 

 

 

The use of dimethyl sulfoxide in the leather industryDimethyl sulfoxide in leather formulations

 

   In experiments with leather tissue, it was found that D MSO greatly enhances the transmission of water through it. For example, the rate of water penetration through the stratum corneum when using dimethyl sulfoxide in solution increases 125 times. It is obvious that dimexide overcomes the skin barrier through the follicles and intercellular spaces.

In addition to its great "transport capacity", dimethyl sulfoxide can form complexes with metal ions with a variable valence, for example, chromium ions, and bind with collagen peptide groups. The described properties of dimethyl sulfoxide make it possible to use it in the process of dressing hides at the stage of processing the skin before the start of chrome tanning and directly in the tanning of the leather itself.It was found during the study that the use of dimexide and its homologon during dressing leads to an improvement in the quality of leather, and a decrease in dressing time. and reducing the chromium oxide content in the spent tanning solution. Leathers, chrome tanned with the use of dimethyl sulfoxide (Dimexide), have better physical, mechanical and hygienic properties, and the content of chromium oxide in the leather increases ..

 

Application of dimethyl sulfoxide in biology

 

    DMSO is used in polymerase chain reaction (PCR) to inhibit the pairing of parental DNA molecules. It is added to the PCR mixture before the start of the reaction, where it interacts with complementary DNA regions, preventing their pairing and reducing the number of side processes.

 

The use of dimethyl sulfoxide in medicine

 

    As a drug, purified dimethyl sulfoxide is used in the form of aqueous solutions (10-50%), as a local anti-inflammatory and analgesic agent, as well as in ointments to increase the transdermal transfer of active substances, since it Dimethyl sulfoxide_chemistry.jpgpenetrates the skin and transfers other substances in a few seconds. The trade name of the drug is "Dimexid".

 

Dimethyl sulfoxide

EC Inventory, Pre-Registration process, Other, Cosmetic Products Regulation, Annex II - Prohibited Substances

dimethyl sulphoxide

FCM and Articles Regulation, Annex I - Authorised Substances

CAS names

Methane, 1,1'-sulfinylbis-

Other

IUPAC names

Dimethyl sulphoxide, anhydrous

C&L Inventory

Dimethylsulfoxid

Registration dossier

Dimethylsulfoxide

C&L Inventory

DMSO, Methyl Sulfoxide

Registration dossier

methanesulfinylmethane

C&L Inventory, Other

Methylsulfinidemethane

C&L Inventory

methylsulfinylmethan

C&L Inventory

methylsulfinylmethane

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