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.]
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)
Bromobenzene may be sensitive to light. May react with oxidizing agents .
Special Hazards of Combustion Products: Irritating hydrogen bromide and other gases may be produced in fire.
Contact with liquid causes irritation of eyes and mild irritation of skin. Ingestion causes mild irritation of mouth and stomach.
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
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.
The Journal of Organic Chemistry, 30, p. 304, 1965 DOI: 10.1021/jo01012a512Tetrahedron Letters, 26, p. 1935, 1985 DOI: 10.1016/S0040-4039(00)98345-X
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.
Air & Water Reactions
Flammable. Insoluble in water.
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.
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
Skin irritant. Moderate fire risk.
Mobile, clear, colorless to pale yellow liquid with an aromatic odor. The reported odor threshold is
4.6 ppm (Mateson, 1955).
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.
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.