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Bromobenzene

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Bromobenzene Basic information

Product Name:
Bromobenzene
Synonyms:
  • Bromobenzene (1mg/ml in Methanol) [for Water Analysis]
  • BROMOBENZENE extrapure
  • BROMOBENZENE extrapure AR
  • Bromobenzene, Reagent Grade
  • Bromobenzene solution
  • Bromobenzene, 99%, pure
  • 3-Bromobenzene
  • 4-Bromobenzene
CAS:
108-86-1
MF:
C6H5Br
MW:
157.01
EINECS:
203-623-8
Product Categories:
  • Organics
  • BENZENE BASED BROMO
  • Analytical Chemistry
  • Standard Solution of Volatile Organic Compounds for Water & Soil Analysis
  • Standard Solutions (VOC)
  • Chemical Class
  • C6Essential Chemicals
  • Aryl
  • Halogenated Hydrocarbons
  • Reagent Plus
  • Routine Reagents
  • A-BAlphabetic
  • Alpha Sort
  • B
  • -
  • Pharmaceutical Intermediates
  • alkyl bromide
  • BI - BZChemical Class
  • Bromo
  • Halogenated
  • Volatiles/ Semivolatiles
Mol File:
108-86-1.mol
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Bromobenzene Chemical Properties

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. 
2-8°C
solubility 
Miscible with diethyl ether, alcohol, carbon tetrachloride, chloroform and benzene.
form 
Liquid
color 
Clear colorless to faintly yellow
Odor
Pleasant.
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)
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference
108-86-1(CAS DataBase Reference)
NIST Chemistry Reference
Benzene, bromo-(108-86-1)
EPA Substance Registry System
Benzene, bromo-(108-86-1)
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Safety Information

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

MSDS

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Bromobenzene Usage And Synthesis

Chemical Properties

colourless liquid

Physical properties

Mobile, clear, colorless to pale yellow liquid with an aromatic odor. The reported odor threshold is 4.6 ppm (Mateson, 1955).

Uses

In organic synthesis, especially to make phenyl magnesium bromide; as solvent, especially for crystallizations on a large scale and where a heavy liquid is desirable; as additive to motor oils.

General Description

Mobile clear colorless liquid with a pungent odor. Flash point 124°F. Denser than water and insoluble in water. Hence sinks in water. Vapors are heavier than air. A skin irritant.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

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

Hazard

Skin irritant. Moderate fire risk.

Health Hazard

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

Health Hazard

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.

Fire Hazard

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

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

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.

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

Biological. In activated sludge, 34.8% of the applied bromobenzene mineralized to carbon dioxide after 5 d (Freitag et al., 1985).
Photolytic. A carbon dioxide yield of 19.7% was achieved when bromobenzene adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985). Irradiation of bromobenzene in air containing nitrogen oxides gave phenol, 4-nitrophenol, 2,4-dinitrophenol, 4- bromophenol, 3-bromonitrobenzene, 3-bromo-2-nitrophenol, 3-bromo-4-nitrophenol, 3-bromo-6-nitrophenol, 2-bromo-4-nitrophenol, and 2,6-dibromo-4-nitrophenol (Nojima et al., 1980).
Chemical/Physical. Bromobenzene will not hydrolyze to any reasonable extent. In the laboratory, no change in concentration was observed after 29 d at 85 °C in 0.1M NaOH and 0.1M HCl (Kollig, 1995).
Augusti et al. (1998) conducted kinetic studies for the reaction of bromobenzene (0.2 mM) and other monocyclic aromatics with Fenton’s reagent (8 mM hydrogen peroxide; [Fe+2] = 0.1 mM) at 25 °C. They reported a reaction rate constant of 0.0740/min.

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.

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.]

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