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Bromobenzene

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Bromobenzene Basic information
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. Store below +30°C.
  • solubility Miscible with diethyl ether, alcohol, carbon tetrachloride, chloroform and benzene.
  • form Liquid
  • color Clear colorless to faintly yellow
  • OdorPleasant.
  • explosive limit0.5-2.5%(V)
  • Water Solubility insoluble. <0.1 g/100 mL at 20.5 ºC
  • Merck 14,1406
  • BRN 1236661
  • Henry's Law Constant2.47 at 25 °C (gas stripping-GC, Shiu and Mackay, 1997)
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
  • InChIKeyQARVLSVVCXYDNA-UHFFFAOYSA-N
  • CAS DataBase Reference108-86-1(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzene, bromo-(108-86-1)
  • EPA Substance Registry SystemBromobenzene (108-86-1)
Safety Information
MSDS
Bromobenzene Usage And Synthesis
  • Chemical Propertiescolourless liquid
  • Physical propertiesMobile, clear, colorless to pale yellow liquid with an aromatic odor. The reported odor threshold is 4.6 ppm (Mateson, 1955).
  • UsesThe 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.
  • UsesIn 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.
  • UsesBromobenzene is a colorless, flammable liquid with a density greater than water and with an aromatic odor. It is synthesized by the reaction of bromide with benzene in the presence of iron powder. It is used for organic synthesis, particularly in the production of the intermediate phenylmagnesium bromide. Bromobenzene is an additive to motor oils and used as a crystallizing solvent. Bromobenzene is used as an ingredient in the manufacture of phencyclidine, a recreational drug.
  • 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
  • General DescriptionMobile 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 ReactionsFlammable. Insoluble in water.
  • Reactivity ProfileBromobenzene may be sensitive to light. May react with oxidizing agents .
  • HazardSkin irritant. Moderate fire risk.
  • Health HazardContact with liquid causes irritation of eyes and mild irritation of skin. Ingestion causes mild irritation of mouth and stomach.
  • Health HazardThe 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 HazardSpecial Hazards of Combustion Products: Irritating hydrogen bromide and other gases may be produced in fire.
  • Chemical ReactivityReactivity 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.
  • Biochem/physiol ActionsBromobenzene induces hepatic necrosis via the formation of a reactive metabolite that arylates vital cellular macromolecules.
  • Safety ProfileModerately 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.
  • SourceNo 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 FateBiological. 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 pathwayBromobenzene 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 MethodsWash 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.]
  • Toxicity evaluationBromobenzene 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.
Bromobenzene Preparation Products And Raw materials
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