1-BROMOHEXANE
1-Bromohexane is widely used in organic synthesis as an alkylating agent, introducing a hexyl group into various molecules and serving as a valuable intermediate for creating a wide range of organic compounds.
1-Bromohexane is utilized in the preparation of pharmaceuticals and organic chemicals, playing a key role in Grignard reactions and the synthesis of bromo-cyclic compounds.
1-Bromohexane, a colorless liquid with a molecular formula of C6H13Br, has a boiling point of 157-158°C and is slightly soluble in water but dissolves readily in many organic solvents.
CAS Number: 111-25-1
EC Number: 203-850-2
Molecular Formula: C6H13Br
Molecular Weight (g/mol): 165.07
Synonyms: 1-BROMOHEXANE, 111-25-1, Hexyl bromide, n-Hexyl bromide, Bromohexane, 1-Hexyl bromide, Hexane, 1-bromo-, Pentane, bromomethyl-, 1-bromo-hexane, 1-BroMohexane--d2, 1-BroMohexane--d4, WVA0FAX7GA, DTXSID4021929, MFCD00000271, NSC-71206, 1-BROMOHEXANE-2,2,3,3,4,4,5,5,6,6,6-D11, 2159-17-3, UNII-WVA0FAX7GA, EINECS 203-850-2, NSC 71206, hexylbromide, n-hexylbromide, 1-hexylbromide, AI3-28588, 6-bromohexane, 1-bromohexan, 1-bromanylhexane, 1 -bromohexane, 1-bromo-n-hexane, Hexane, 1-bromo, 1-Bromohexane, 98%, 1-bromo-5-methylpentane, EC 203-850-2, NCIOpen2_000490, SCHEMBL33363, DTXCID101929, CHEMBL3187491, NSC71206, Tox21_202719, BBL012217, STL163558, AKOS000118767, NCGC00260267-01, BP-31175, CAS-111-25-1, VS-03238, 1-Bromohexane, purum, >=98.0% (GC), DB-003859, B0600, FT-0607533, EN300-19402, A802329, J-504466, Q3292844, F0001-0236, 111-25-1 [RN], 1-Bromhexan [German] [ACD/IUPAC Name], 1-Bromohexane [ACD/IUPAC Name], 1-Bromohexane [French] [ACD/IUPAC Name], 203-850-2 [EINECS], Hexane, 1-bromo- [ACD/Index Name], Hexyl bromide, MO0925000, [111-25-1] [RN], 1219802-83-1 [RN], 130131-94-1 [RN], 192863-46-0 [RN], 1-bromanylhexane, 1-Bromo-1,1-dideuteriohexane, 1-Bromo-hexane, 1-Bromohexane-1,1,2,2-d4, 1-Bromohexane-1,1-d2, 1-Bromohexane-2,2,3,3,4,4,5,5,6,6,6-d11, 1-Bromohexane-4,4,5,5,6,6,6-d7, 1-Bromohexane-6,6,6-d3, 1-Bromohexane-d13, 1-BroMohexane--d4, 1-bromo-hexano [Portuguese], 1-Hexyl bromide, 2159-17-3 [RN], 25495-91-4 [RN], 350818-70-1 [RN], 78904-38-8 [RN], bromohexane [Wiki], EINECS 203-850-2, Hexane, 1-bromo, hexane, bromo-, HexylBromide, Labotest-bb ltbb001158, MO 0925000, n-Hexyl Bromide, n-hexylbromide, Pentane, bromomethyl-, VS-03238
1-Bromohexane is a colorless to pale yellow liquid with a molecular formula of C6H13Br and a molecular weight of 137.08 g/mol.
Commonly referred to as hexyl bromide, 1-Bromohexane features a straightforward structure consisting of a six-carbon chain with a bromine atom attached to the first carbon.
With a boiling point of 157-158°C and a melting point of -112.7°C, 1-Bromohexane is a relatively low-melting, moderately high-boiling compound.
1-Bromohexane's density is approximately 1.11 g/mL at 20°C, and it has a vapor density of 4.7, indicating it is denser than air.
The vapor pressure of 1-bromohexane is 10 mm Hg at 20°C, reflecting its volatility
1-Bromohexane is slightly soluble in water but dissolves readily in many organic solvents, making it useful in various chemical reactions and as an intermediate in organic synthesis.
The refractive index is around 1.453, and the flash point is 40°C, which suggests 1-Bromohexane should be handled with care to avoid ignition sources.
1-Bromohexane is commonly used in the preparation of other chemicals and as a reagent in organic chemistry.
1-Bromohexane's stability and storage requirements involve keeping it in a cool, dry place to maintain its integrity.
1-Bromohexane is an organic compound with the chemical formula C6H13Br.
1-Bromohexane is a colorless to slightly yellow liquid that belongs to the class of alkyl halides, where a bromine atom is bonded to an alkyl chain.
1-Bromohexane is organobromine compound with formula Br(CH2)5CH3.
1-Bromohexane is a colorless liquid.
1-Bromohexane is utilized in the preparation of pharmaceuticals and organic chemicals.
1-Bromohexane is involved in Grignard reactions as an alkylating agent and in the synthesis of bromo-cyclic compounds.
1-Bromohexane is an organic compound with the molecular formula C6H13Br.
1-Bromohexane is a colorless liquid that is widely used in organic synthesis, mainly as a reagent for the formation of alkyl bromides.
Due to 1-Bromohexane low boiling point.
1-bromohexane is also used as a solvent in many industrial and laboratory applications.
1-Bromohexane is a widely used precursor in the synthesis of a variety of organic compounds.
Uses of 1-Bromohexane:
1-Bromohexane is used to manufacture pharmaceuticals and organic chemicals.
Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.
1-Bromohexane is utilized in the preparation of pharmaceuticals and organic chemicals.
1-Bromohexane is involved in Grignard reactions as an alkylating agent and in the synthesis of bromo-cyclic compounds.
1-Bromohexane is a very useful synthetic intermediate.
1-Bromohexane can be used to react with Mg to prepare Grignard reagents which play an important role in formation of carbon-carbon bond.
1-Bromohexane has several important uses, particularly in organic synthesis and industrial applications.
Here’s a detailed look at 1-Bromohexane's primary uses:
Alkylating Agent in Organic Synthesis:
1-Bromohexane is commonly used as an alkylating agent in organic synthesis.
1-Bromohexane introduces a hexyl group into various molecules, making it a valuable intermediate for creating a wide range of organic compounds.
For example:
Pharmaceuticals:
1-Bromohexane can be used to synthesize complex drug molecules where the introduction of a hexyl group is necessary.
Agrochemicals:
In the production of pesticides and herbicides, 1-bromohexane helps build long-chain alkyl structures.
Fragrances and Flavors:
1-Bromohexane can be used to synthesize specific compounds with hexyl chains, which might be components of fragrances or flavoring agents.
Preparation of Grignard Reagents:
1-Bromohexane is used in the preparation of Grignard reagents, such as hexylmagnesium bromide.
Grignard reagents are key intermediates in forming carbon-carbon bonds, enabling the synthesis of alcohols, acids, ketones, and other organic molecules.
Reaction Example:
C6H13Br+Mg→C6H13MgBr
1-Bromohexane can then react with various electrophiles to form new carbon-carbon bonds.
Surfactant Synthesis:
1-Bromohexane can be used in the synthesis of surfactants, which are compounds that lower the surface tension between two liquids or between a liquid and a solid.
Surfactants are essential in products like detergents, emulsifiers, and wetting agents.
The hexyl group introduced by 1-bromohexane contributes to the hydrophobic tail of the surfactant molecule.
Polymer and Material Science:
In polymer chemistry, 1-bromohexane can be used to modify or functionalize polymers.
Introducing hexyl groups into polymers can alter their physical properties, such as solubility, flexibility, or hydrophobicity, making them suitable for specific industrial applications.
Intermediate in Chemical Synthesis:
1-Bromohexane serves as an intermediate in the synthesis of various chemicals.
For instance:
Organometallic Compounds:
Besides Grignard reagents, 1-bromohexane can be used to prepare other organometallic compounds that are pivotal in various catalytic and synthetic processes.
Specialty Chemicals:
1-Bromohexane is used in the manufacture of specialty chemicals where the introduction of a hexyl group is required.
Research and Development:
In research laboratories, 1-bromohexane is used in various experimental setups to study chemical reactions, particularly in the study of substitution and elimination reactions.
1-Bromohexanes also used in the development of new synthetic routes for complex molecules.
Cross-Coupling Reactions
1-Bromohexane can participate in cross-coupling reactions, such as the Suzuki or Heck reactions, to create new carbon-carbon bonds.
This is useful in the synthesis of complex organic structures, including biaryl compounds, which are important in pharmaceuticals and organic materials.
Synthesis of Hexyl Derivatives
1-Bromohexanes employed to synthesize various hexyl derivatives, which are important in different industries.
These derivatives might include hexylamines, hexyl alcohols, or hexyl esters, which are used in everything from solvents to plasticizers.
Chemical Properties of 1-Bromohexane:
1-Bromohexane is a colourless liquid organohalide.
1-Bromohexane is a solvent that is frequently used in grignard reactions.
1-Bromohexane is also used as Intermediate, for introduction of hexyl group.
Chemical Nature of 1-Bromohexane:
1-Bromohexane is organobromine compound with formula Br(CH2)5CH3.
1-Bromohexane is a colorless liquid.
Synthesis and Reactions of 1-Bromohexane:
Most 1-bromoalkanes are prepared by free-radical addition of hydrogen bromide to the 1-alkene.
These conditions lead to anti-Markovnikov addition, giving the 1-bromo derivative.
1-Bromohexane undergoes reactions expected of simple alkyl bromides.
1-Bromohexane can form Grignard reagents.
1-Bromohexane reacts with potassium fluoride to give the corresponding fluorocarbons.
Synthesis:
1-Bromohexane can be synthesized in several ways.
One of the most common methods is the nucleophilic substitution reaction of hexane with bromine in the presence of a Lewis acid catalyst.
This reaction is usually carried out in an inert atmosphere, such as nitrogen or argon, to prevent oxidation of the bromine.
Another method for the synthesis of 1-bromohexane is the direct addition of bromine to hexane.
This reaction is usually carried out in the presence of a radical initiator, such as t-butyl hydroperoxide, to generate the bromine radical.
Action Mechanism of 1-Bromohexane:
1-Bromohexane is a nucleophilic reagent, which means that 1-Bromohexane reacts with electrophiles (electron-rich molecules) to form a new bond.
In the synthesis of alkyl bromides, 1-bromohexane reacts with the electrophilic carbon atom of the alkyl halide to form a new carbon-bromine bond.
This reaction is usually catalyzed by a Lewis acid, such as aluminum chloride or boron trifluoride.
Biochemical and Physiological Effects of 1-Bromohexane:
1-Bromohexane is not known to have any biochemical or physiological effects.
1-Bromohexane is considered to be non-toxic and is not believed to be a carcinogen.
However, 1-Bromohexane is important to note that 1-Bromohexane is a flammable liquid and should be handled with care.
Advantages and Limitations for Lab Experiments of 1-Bromohexane:
1-Bromohexane has several advantages for use in laboratory experiments.
1-Bromohexane is a relatively inexpensive reagent and is readily available in many chemical supply stores.
1-Bromohexane is also a low boiling point solvent, which makes 1-Bromohexane ideal for use in reactions that require low temperature conditions.
In addition, 1-Bromohexane is a relatively non-toxic compound and is not believed to be a carcinogen.
However, 1-bromohexane has several limitations for use in laboratory experiments.
1-Bromohexane is a flammable liquid and should be handled with care.
1-Bromohexane is also volatile and has a low flash point, which means that 1-Bromohexane can ignite easily.
In addition, 1-Bromohexane can react with other compounds in the presence of a catalyst, so 1-Bromohexane should not be used in reactions that require a high degree of selectivity.
Future Directions of 1-Bromohexane:
1-Bromohexane has a wide range of potential applications in the synthesis of organic compounds.
In the future, 1-Bromohexane could be used as a precursor in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals.
In addition, 1-Bromohexane could be used as a reagent in the synthesis of polymers, such as poly(vinyl chloride), poly(ethylene terephthalate), and poly(vinyl acetate).
1-Bromohexane could also be used as a solvent in organic reactions, such as the synthesis of alkyl bromides.
Finally, 1-bromohexane could be used in the synthesis of other organic compounds, such as alcohols, amines, and carboxylic acids.
Handling and Storage of 1-Bromohexane:
Advice on protection against fire and explosion:
Keep away from open flames, hot surfaces and sources of ignition.
Take precautionary measures against static discharge.
Hygiene measures:
Immediately change contaminated clothing.
Apply preventive skin protection.
Wash hands and face after working with 1-Bromohexane.
Conditions for safe storage, including any incompatibilities:
Storage conditions:
Keep container tightly closed in a dry and well-ventilated place.
Keep away from heat and sources of ignition.
Storage class:
Storage class (TRGS 510): 3: Flammable liquids
Stability and Reactivity of 1-Bromohexane:
Reactivity:
Vapor/air-mixtures are explosive at intense warming.
Chemical stability:
1-Bromohexane is chemically stable under standard ambient conditions (room temperature).
Conditions to avoid:
Heating.
Incompatible materials:
Strong oxidizing agents, Strong bases
Hazardous decomposition products:
In the event of fire
First Aid Measures of 1-Bromohexane:
General advice:
Show 1-Bromohexane safety data sheet to the doctor in attendance.
After inhalation:
Fresh air.
In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
Most important symptoms and effects, both acute and delayed:
The most important known symptoms and effects are described in the labelling.
Firefighting Measures of 1-Bromohexane:
Suitable extinguishing media:
Water Foam Carbon dioxide (CO2) Dry powder
Unsuitable extinguishing media:
For 1-Bromohexane no limitations of extinguishing agents are given.
Special hazards arising from 1-Bromohexane or mixture:
Carbon oxides
Hydrogen bromide gas
Vapors are heavier than air and may spread along floors.
Forms explosive mixtures with air at elevated temperatures.
Development of hazardous combustion gases or vapours possible in the event of fire.
Advice for firefighters:
Stay in danger area only with self-contained breathing apparatus.
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.
Further informations:
Remove container from danger zone and cool with water.
Suppress (knock down) gases/vapors/mists with a water spray jet.
Prevent fire extinguishing water from contaminating surface water or the ground water system.
Accidental Release Measures of 1-Bromohexane:
Advice for non-emergency personnel:
Do not breathe vapors, aerosols.
Avoid substance contact.
Ensure adequate ventilation.
Keep away from heat and sources of ignition.
Evacuate the danger area, observe emergency procedures, consult an expert.
Environmental precautions:
Do not let product enter drains.
Risk of explosion.
Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up with liquid-absorbent material (e.g. Chemizorb).
Dispose of properly.
Clean up affected area.
Identifiers of 1-Bromohexane:
CAS Number: 111-25-1
Beilstein Reference: 1731290
ChemSpider: 7810
ECHA InfoCard: 100.003.501
EC Number: 203-850-2
MeSH: 1-bromohexane
PubChem CID: 8101
RTECS number: MO0925000
UNII: WVA0FAX7GA
UN number: 1993
CompTox Dashboard (EPA): DTXSID4021929
InChI: InChI=1S/C6H13Br/c1-2-3-4-5-6-7/h2-6H2,1H3
Key: MNDIARAMWBIKFW-UHFFFAOYSA-N
SMILES: CCCCCCBr
CAS number: 111-25-1
EC number: 203-850-2
Hill Formula: C₆H₁₃Br
Chemical formula: CH₃(CH₂)₅Br
Molar Mass: 165.08 g/mol
HS Code: 2903 69 19
Synonym(s): Hexyl bromide
Linear Formula: CH3(CH2)5Br
CAS Number: 111-25-1
Molecular Weight: 165.07
Beilstein: 1731290
EC Number: 203-850-2
MDL number: MFCD00000271
PubChem Substance ID: 24891825
NACRES: NA.22
CAS: 111-25-1
Molecular Formula: C6H13Br
Molecular Weight (g/mol): 165.07
MDL Number: MFCD00000271
InChI Key: MNDIARAMWBIKFW-UHFFFAOYSA-N
PubChem CID: 8101
IUPAC Name: 1-bromohexane
SMILES: CCCCCCBr
Properties of 1-Bromohexane:
Chemical formula: C6H13Br
Molar mass: 165.074 g·mol−1
Appearance: Colorless liquid
Density: 1.176 g/mL
Melting point: −84.70 °C; −120.46 °F; 188.45 K
Boiling point: 154 to 158 °C; 309 to 316 °F; 427 to 431 K
Solubility in water: Insoluble
Solubility: Alcohol, ether
Refractive index (nD): 1.448 (20 °C, D)
Density: 1.18 g/cm3 (20 °C)
Flash point: 57 °C
Melting Point: -85 °C
Vapor pressure: 4 hPa (20 °C)
Solubility: <1 g/l
Vapor density: 5.7 (vs air)
Quality Level: 200
Vapor pressure: <10 mmHg ( 20 °C)
Assay: 98%
Form: liquid
Refractive index: n20/D 1.448 (lit.)
bp: 154-158 °C (lit.)
mp: −85 °C (lit.)
Density: 1.176 g/mL at 25 °C (lit.)
SMILES string: CCCCCCBr
InChI: 1S/C6H13Br/c1-2-3-4-5-6-7/h2-6H2,1H3
InChI key: MNDIARAMWBIKFW-UHFFFAOYSA-N
Molecular Weight: 165.07 g/mol
XLogP3: 3.8
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 4
Exact Mass: 164.02006 g/mol
Monoisotopic Mass: 164.02006 g/mol
Topological Polar Surface Area: 0Ų
Heavy Atom Count: 7
Complexity: 27.4
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Thermochemistry of 1-Bromohexane:
Heat capacity (C): 219.7 J K−1 mol−1
Std molar entropy (S⦵298): 452.92 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298): −196.1–−192.9 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298): −4026.2–−4023.0 kJ mol−1
Specifications of 1-Bromohexane:
Assay (GC, area%): ≥ 98.0 % (a/a)
Density (d 20 °C/ 4 °C): 1.174 - 1.176
Identity (IR): passes test
Acidity: 0.1% max. (as HBr)
CAS Min %: 99.0
CAS Max %: 100.0
Melting Point: -85°C
Density: 1.1700g/mL
Boiling Point: 154°C to 158°C
Flash Point: 57°C
Infrared Spectrum: Authentic
Assay Percent Range: 0.5% max. Hexanol (GC)
Packaging: Glass bottle
Linear Formula: CH3(CH2)5Br
Refractive Index: 1.4465 to 1.4485
Quantity: 500 mL
Beilstein: 01,144
Specific Gravity: 1.17
Solubility Information: Solubility in water: insoluble
Formula Weight: 165.07
Percent Purity: 99+%
Physical Form: Liquid
Chemical Name or Material: 1-Bromohexane
Related compounds of 1-Bromohexane:
Related alkanes:
1-Bromobutane
1-Bromododecane
2-Bromobutane
2-Bromohexane
Related Products of 1-Bromohexane:
Dimethyl Glutaconate (~10% Cis)
(E,E)-4,6-Dimethyl-2,4-heptadienoic Acid
3,6-Dimethyl-3-heptanol
1,1-Dimethoxybutane
(E)-6,6-Dimethyl-2-hept-1-en-4-yn-1-amine
Names of 1-Bromohexane:
Preferred IUPAC name:
1-Bromohexane
Other names:
Bromohexane
Hexyl bromide}
1-Hexyl bromide
n-Hexyl bromide
