ChemicalBook > CAS DataBase List > Bromobenzene

Bromobenzene

Product Name
Bromobenzene
CAS No.
108-86-1
Chemical Name
Bromobenzene
Synonyms
1-Bromobenzene;Brombenzol;PHENYL BROMIDE;4-Bromobenzene;NCI-C55492;Bromobenzol;romobenzene;bromo-benzen;BROMOBENZENE;Benzene,bromo-
CBNumber
CB6235569
Molecular Formula
C6H5Br
Formula Weight
157.01
MOL File
108-86-1.mol
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Bromobenzene Property

Melting point:
-31 °C
Boiling point:
156 °C(lit.)
Density 
1.491 g/mL at 25 °C(lit.)
vapor density 
5.41 (vs air)
vapor pressure 
10 mm Hg ( 40 °C)
refractive index 
n20/D 1.559(lit.)
Flash point:
124 °F
storage temp. 
Store below +30°C.
solubility 
Miscible with diethyl ether, alcohol, carbon tetrachloride, chloroform and benzene.
form 
Liquid
color 
Clear colorless to faintly yellow
Odor
pleasant smell
explosive limit
0.5-2.5%(V)
Water Solubility 
insoluble. <0.1 g/100 mL at 20.5 ºC
Merck 
14,1406
BRN 
1236661
Henry's Law Constant
2.47 at 25 °C (gas stripping-GC, Shiu and Mackay, 1997)
Dielectric constant
5.4（20℃）
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
QARVLSVVCXYDNA-UHFFFAOYSA-N
LogP
3.14 at 25℃
Surface tension
33.5mN/m at 303.15K
CAS DataBase Reference
108-86-1(CAS DataBase Reference)
NIST Chemistry Reference
Benzene, bromo-(108-86-1)
EPA Substance Registry System
Bromobenzene (108-86-1)
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Safety

Hazard Codes 
Xi,N,F,T
Risk Statements 
10-38-51/53-39/23/24/25-23/24/25
Safety Statements 
61-45-36/37
RIDADR 
UN 2514 3/PG 3
WGK Germany 
2
RTECS 
CY9000000
Autoignition Temperature
565 °C
TSCA 
Yes
HS Code 
2903 99 80
HazardClass 
3
PackingGroup 
III
Hazardous Substances Data
108-86-1(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 2383 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P273Avoid release to the environment.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.01786
Product name
Bromobenzene
Purity
for synthesis
Packaging
5ml
Price
$31.2
Updated
2025/07/31
Sigma-Aldrich
Product number
8.01786
Product name
Bromobenzene
Purity
for synthesis
Packaging
250ML
Price
$37.3
Updated
2025/07/31
Sigma-Aldrich
Product number
8.01786
Product name
Bromobenzene
Purity
for synthesis
Packaging
1L
Price
$141
Updated
2025/07/31
Sigma-Aldrich
Product number
8.01786
Product name
Bromobenzene
Purity
for synthesis
Packaging
25L
Price
$3320
Updated
2025/07/31
Sigma-Aldrich
Product number
16350
Product name
Bromobenzene
Purity
≥99.5% (GC)
Packaging
100ml
Price
$45
Updated
2025/07/31
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Bromobenzene Chemical Properties,Usage,Production

Description

Bromobenzene is a flammable, clear, colorlessmobile liquid with a pleasant odor. Molecularweight=157.02. Specific gravity (H2O:1)=1.48; Boilingpoint=156℃; Freezing/Melting point=2 31℃; Flashpoint=51℃; Autoignition temperature=565℃. Explosivelimits in air: LEL=6%; UEL=36.5%[icsc]. HazardIdentification (based on NFPA-704 M Rating System):Health 2, Flammability 2, Reactivity 0. Very slightly soluble in water; solubility=0.04% at 25℃.

Chemical Properties

Bromobenzene, also known as phenyl bromide and monobromobenzene, is a benzene halogen derivative generated by benzene being substituted by bromine in the presence of iron powder. The chemical reaction principle is the same as that of chlorination of benzene to produce chlorobenzene. The reaction between bromobenzene and metal magnesium can generate phenylmagnesium bromide, which is a Grignard reagent with important uses in organic synthesis.

Physical properties

Mobile, clear, colorless to pale yellow liquid with an aromatic odor. The reported odor threshold is 4.6 ppm (Mateson, 1955). Insoluble in water, soluble in benzene, alcohol, ether, chlorobenzene and other organic solvents. It is irritating to the skin and anesthetic to the nerves. Its toxicity is stronger than chlorobenzene. Inhalation of its vapors can cause anemia and damage the liver.

Uses

Bromobenzene is an additive to motor oils and used as a crystallizing solvent. It is used as an ingredient in the manufacture of phencyclidine, a recreational drug.

Definition

ChEBI: Bromobenzene is the simplest member of the class of bromobenzenes, that is benzene in which a single hydrogen has been substituted by a bromine. A liquid at room temperature (m.p. -30℃; b.p.760 156℃), it is used as a solvent, particularly for large-scale crystallisations, and for the introduction of phenyl groups in organic synthesis. It has a role as a non-polar solvent, a hepatotoxic agent and a mouse metabolite. It is a member of bromobenzenes, a bromoarene and a volatile organic compound.

Application

The compound is employed as a starting material in organic syntheses in which a Grignard intermediate (phenyl magnesium bromide) is used. The material is a chemical precursor for certain agricultural products and has been used as an additive to motor oils. Bromobenzene has also been used as a high-density solvent for chemical recrystallization processes. especially for crystallizations on a large scale and where a heavy liquid is desirable.

Preparation

Bromobenzene is obtained by reacting benzene with bromine. First add iron powder and benzene into the reactor, slowly add bromine under stirring, keep the reaction at 70-80°C for 1 h after adding, the obtained crude product is washed with water and 5% sodium hydroxide solution, left to stand for stratification, distillation, Drying, filtering, and finally fractional distillation under constant pressure, taking the fraction at 155-157°C to obtain the finished product.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 304, 1965 DOI: 10.1021/jo01012a512
Tetrahedron Letters, 26, p. 1935, 1985 DOI: 10.1016/S0040-4039(00)98345-X

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

Bromobenzene may be sensitive to light. May react with oxidizing agents .

Health Hazard

Contact with Bromobenzene liquid causes irritation of eyes and mild irritation of skin. Ingestion causes mild irritation of mouth and stomach.

Fire Hazard

Moderate fire risk. Special Hazards of Combustion Products: Irritating hydrogen bromide and other gases may be produced in fire.

Biochem/physiol Actions

Bromobenzene induces hepatic necrosis via the formation of a reactive metabolite that arylates vital cellular macromolecules.

Safety Profile

Moderately toxic by ingestion, subcutaneous, and intraperitoneal routes. LWdly toxic by inhalation. An eye and mucous membrane irritant. Mutation data reported. Flammable liquid when exposed to heat, sparks, or flame. Can react with oxidtzing materials. To fight fire, use water to blanket fire, foam, CO2, water spray or mist, dry chemical. Violent reaction with bromobutane + sodium when heated above 30℃. When heated to decomposition it emits toxic fumes of Br-. See also BROMIDES.

Potential Exposure

Mutagen.Bromobenzene is used as an intermediate in organic synthesis,and as an additive in motor oil and fuels. During chlorination water treatment, bromobenzene can be formed insmall quantities.

First aid

If Bromobenzene gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seekmedical attention immediately. If this chemical contactsthe skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately.   If this chemical has been inhaled, remove fromexposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing hasstopped and CPR if heart action has stopped. Transferpromptly to a medical facility. When this chemical hasbeen swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

Source

No MCLs, MCLGs, or DWELs have been proposed (U.S. EPA, 2000).
Storm water runoff, waste motor oils, improper disposal of laboratory solvent containing bromobenzene (quoted, Verschueren, 1983)

Environmental Fate

Bromobenzene will volatilize from dry surfaces, due to its vapor pressure of 4.18mmHg at 25°C, and therefore will exist as a vapor in the environment. Bromobenzene will undergo little hydrolysis in water and little biodegradation by aquatic microorganisms. Bromobenzene is not expected to adsorb to sediment from water due to its soil sorption constant (Koc) of 150 and water solubility of 446 mg l-1. It is also expected to have a high mobility in soil and volatilize easily from moist surfaces due to its Henry’s law constant of 2.47×10-3 atmm3 mol-1 at 25°C. Bioconcentration factors range from low values of 8.8 in carp to moderately high values of 190 in algae.

Metabolic pathway

Bromobenzene and chlorobenzene are metabolized by human and mouse hepatic microsomes to two different epoxide intermediates, which rearrange to form either o- or p-bromo- and o- or p-chlorophenols, respectively. Humans preferentially metabolize halobenzenes through the hepatotoxic 3,4-epoxide pathway, suggesting that humans may be more susceptible than mice to halobenzene-induced hepatotoxicity.

storage

Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with bromobenzene you should be trainedon its proper handling and storage. Store in tightly closedcontainers in a refrigerated area away from incompatiblematerials listed above. Protect from light. Metal containers involving the transfer of this chemical should begrounded and bonded. Drums must be equipped with selfclosing valves, pressure vacuum bungs, and flame arresters.Use only nonsparking tools and equipment, especiallywhen opening and closing containers of this chemical.Sources of ignition, such as smoking and open flames, areprohibited where this chemical is used, handled, or storedin a manner that could create a potential fire or explosionhazard.

Shipping

Bromobenzene requires a “FLAMMABLELIQUID” label. It falls in Hazard Class 3 and PackingGroup II.

Purification Methods

Wash bromobenzene vigorously with conc H2SO4, then 10% NaOH or NaHCO3 solutions, and H2O. Dry it with CaCl2 or Na2SO4, or pass it through activated alumina, before refluxing with, and distilling from, CaH2, using a glass helix-packed column. [Beilstein 5 IV 670.]

Toxicology

The acute toxicity of bromobenzene is lowin test animals. The toxic symptoms includesomnolence, respiratory stimulation, and muscle contraction. The oral LD50 value in rats is2700 mg/kg.

Incompatibilities

Forms explosive mixture with air.Incompatible with strong oxidizers, alkaline earth metals(barium, calcium, magnesium, strontium, etc.), metallicsalts; with risk of violent reactions. May accumulate staticelectrical charges; may cause ignition of its vapors.

Toxics Screening Level

The initial threshold screening level (ITSL) for bromobenzene is 60 μg/m3 based on an annual averaging time.

Bromobenzene Preparation Products And Raw materials

Raw materials

Bromine

Preparation Products

Nimesulide 2-(HYDROXYETHYL)-6-METHYLPYRIDINE (-)-Taddol 1-Bromo-4-(trifluoromethoxy)benzene Phenylsilane Ethyl N-(diphenylmethylene)glycinate PHENYLSELENOL 1-Bromo-4-nitrobenzene 1-Phenylimidazole 4-Bromobenzenesulfonamide N-Phenylanthranilic acid Butylbenzene Diphenyl(4-pyridyl)methanol Ethyl benzoylformate 3-PHENYLBUTYRIC ACID CLOTRIMAZOLE IMP. A (PHARMEUROPA): (2-CHLOROPHENYL)DIPHENYLMETHANOL DOXEPIN 1,3-DIMETHYL-4-PHENYL-4-PIPERIDINOL 4-Bromo-2,2-diphenylbutyric acid Sodium tetraphenylboron Phenyltriethoxysilane 4-N-OCTYLBENZALDEHYDE Triphenyltin acetate ISOPROPYLDIPHENYLPHOSPHINE (+)-Taddol 4-Phenoxyphenol 4-Bromomandelic acid 2-PHENYLBENZYLAMINE HYDROCHLORIDE 3-CHLORO-2-METHYLBIPHENYL Triclosan ALPHA,ALPHA-DIPHENYL-GAMMA-BUTYROLACTONE 2-Phenylquinoline brofluthrinate brofenvalerate 2-METHOXYACETOPHENONE 9-phenylanthracene Diphenyl diselenide Allylbenzene p-Terphenyl 2-Chlorotrityl chloride
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View Lastest Price from Bromobenzene manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
Bromobenzene 108-86-1
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-10-25
Hebei Yanxi Chemical Co., Ltd.
Product
bromobenzene 108-86-1
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20tons
Release date
2023-10-13
Hebei Chuanghai Biotechnology Co,.LTD
Product
bromobenzene 108-86-1
Price
US $19.00/KG
Min. Order
1KG
Purity
99.%
Supply Ability
10 ton
Release date
2024-08-15

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