Bromobenzene Chemical Properties
- Melting point:
- -31 °C
- Boiling point:
- 156 °C(lit.)
- 1.491 g/mL at 25 °C(lit.)
- vapor density
- 5.41 (vs air)
- vapor pressure
- 10 mm Hg ( 40 °C)
- refractive index
- Flash point:
- 124 °F
- storage temp.
- Miscible with diethyl ether, alcohol, carbon tetrachloride, chloroform and benzene.
- Clear colorless to faintly yellow
- explosive limit
- Water Solubility
- insoluble. <0.1 g/100 mL at 20.5 ºC
- Henry's Law Constant
- 2.47 at 25 °C (gas stripping-GC, Shiu and Mackay, 1997)
- 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
- Bromobenzene (108-86-1)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 2514 3/PG 3
- WGK Germany
- Autoignition Temperature
- 565 °C
- HS Code
- 2903 99 80
- Hazardous Substances Data
- 108-86-1(Hazardous Substances Data)
- LD50 orally in Rabbit: 2383 mg/kg
Bromobenzene Usage And Synthesis
Mobile, clear, colorless to pale yellow liquid with an aromatic odor. The reported odor threshold is 4.6 ppm (Mateson, 1955).
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.
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.
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.
Bromobenzene may be sensitive to light. May react with oxidizing agents .
Skin irritant. Moderate fire risk.
Contact with liquid causes irritation of eyes and mild irritation of skin. Ingestion causes mild irritation of mouth and stomach.
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.
Special Hazards of Combustion Products: Irritating hydrogen bromide and other gases may be produced in fire.
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.
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.
No MCLs, MCLGs, or DWELs have been proposed (U.S. EPA,
Storm water runoff, waste motor oils, improper disposal of laboratory solvent containing bromobenzene (quoted, Verschueren, 1983)
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.
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.
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.]
Bromobenzene Preparation Products And Raw materials
- (R)-2-HYDROXY-2-METHYL(3-BROMOBENZENE)PROPANOIC ACID
- (R)-2-HYDROXY-2-METHYL(4-BROMOBENZENE)ACETIC ACID
- ETHYL (R)-2-HYDROXY-2-METHYL(2-BROMOBENZENE)PROPANOATE
- (S)-2-HYDROXY-2-METHYL(3-BROMOBENZENE)PROPANOIC ACID
- (S)-2-HYDROXY-2-METHYL(3-BROMOBENZENE)ACETIC ACID
- (R)-2-HYDROXY-2-METHYL(4-BROMOBENZENE)PROPANOIC ACID
- (R)-2-HYDROXY-2-METHYL(2-BROMOBENZENE)PROPANOIC ACID
- ETHYL (R)-2-HYDROXY-2-METHYL(4-BROMOBENZENE)PROPANOATE
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