BROMOBENZENE

BROMOBENZENE Synonyms: AI3-09059; BrBz; BRN 1236661; Benzene bromide; Bromobenzol; CCRIS 5887; EINECS 203-623-8; Monobromobenzene; Monobromobenzol; NCI-C55492; NSC 6529; Phenyl bromide; UN 2514.

Br

CASRN: 108-86-1; DOT: 2514; DOT label: Flammable liquid; molecular formula: C6H5Br; FW: 157.01; RTECS: CY9000000; Merck Index: 12, 1427 Physical state, color, and odor: Mobile, clear, colorless to pale yellow liquid with an aromatic odor. The reported odor threshold is 4.6 ppm (Mateson, 1955). Melting point (°C): -30.8 (Weast, 1986) Boiling point (°C): 155.86 (Artigas et al., 1997) Density (g/cm3): 1.5017 at 15 °C (Windholz et al., 1983) 1.49466 at 20.00 °C (Tsierkezos et al., 2000) 1.48818 at 25.00 °C (Artigas et al., 1997) 1.48147 at 30.00 °C (Ramadevi et al., 1996) 1.4730 at 35.00 °C (Nayak et al., 2003) Diffusivity in water (x 10-5 cm2/sec at 25 °C): 1.03 (x = 10-6), 0.99 (x = 2 x 10-6), 0.96 (x = 5 x 10-6) (Gabler et al., 1996) Flash point (°C): 51 (Windholz et al., 1983) Entropy of fusion (cal/mol⋅K): 10.55 (Masi and Scott, 1975) Heat of fusion (kcal/mol): 2.54 (Dean, 1987) Henry’s law constant (x 10-3 atm⋅m3/mol): 2.527, 3.277, and 5.685 at 30.0, 35.0, and 44.8 °C, respectively (variable headspace method,

Hansen et al., 1993, 1995) 0.91 at 10.00 °C, 1.65 at 20.00 °C, 2.76 at 30.00 °C, 4.24 at 40.00 °C, 6.02 at 50.00 °C (inert gas

stripping, Hovorka and Dohnal, 1997) 2.47 at 25 °C (gas stripping-GC, Shiu and Mackay, 1997) Interfacial tension with water (dyn/cm): 38.1 at 25 °C (Donahue and Bartell, 1952) 39.30 at 20 °C, 37.96 at 40 °C, 36.30 at 60 °C, 34.33 at 80 °C (Jasper and Wood, 1955)

8.98 ± 0.02 (Franklin et al., 1969) 9.41 (quoted, Yoshida et al., 1983) Bioconcentration factor, log BCF: 3.18 (activated sludge), 2.28 (algae), 1.70 (golden ide) (Freitag et al., 1985) Soil organic carbon/water partition coefficient, log Koc: 2.65 (estimated from HPLC capacity factors, Hodson and Williams, 1988) Octanol/water partition coefficient, log Kow: 2.75 and 2.94 at 25 and 60 °C, respectively (shake flask-UV spectrophotometry, Kramer and

Henze, 1990) 3.15 (estimated from HPLC capacity factors, Eadsforth, 1986) 3.01 at 25 °C (generator column-HPLC, Garst, 1984; RP-HPLC, Garst and Wilson, 1984; shake

flask-GC, Watarai et al., 1982) 2.99 at 25 °C (shake flask-UV, Fujita et al., 1964; shake flask-GLC, Hansch and Anderson, 1967) 2.96 (Kenaga and Goring, 1980) 2.98 (generator column-HPLC/GC, Wasik et al., 1981, 1983; generator column, Doucette and

Andren, 1988) Solubility in organics: At 25 °C (wt %): alcohol (10.4) and ether (71.3). Miscible with benzene, chloroform, petroleum ethers (Windholz et al., 1983), and many other organic solvents (Patnaik, 1992). Solubility in water: 500 mg/L at 20 °C (quoted, Verschueren, 1983) 446 mg/L at 30 °C (Chiou et al., 1977) 446 mg/kg at 30 °C (shake flask-interferometer, Gross and Saylor, 1931) 410 mg/L at 25 °C (shake flask-UV spectrophotometry, Andrews and Keefer, 1950) 2.92 mM at 35 °C (Hine et al., 1963) 2.3 mM at 25 °C (shake flask-UV spectrophotometry, Yalkowsky et al., 1979) 2.62 mM at 25 °C (generator column-HPLC/GC, Wasik et al., 1981, 1983) 2.84 mmol/kg at 25.0 °C (shake flask-UV spectrophotometry, Vesala, 1974) Vapor density: 6.42 g/L at 25 °C, 5.41 (air = 1) Vapor pressure (mmHg): 3.3 at 20 °C (quoted, Verschueren, 1983) 3.8 at 25 °C (quoted, Valsaraj, 1988) 4.14 at 25 °C (quoted, Mackay et al., 1982) 7.48 at 35 °C (Hine et al., 1963) 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, 4bromophenol, 3-bromonitrobenzene, 3-bromo-2-nitrophenol, 3-bromo-4-nitrophenol, 3-bromo-6-

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. Toxicity: Acute oral LD50 for rats 2,699 mg/kg, mice 2,700 mg/kg (quoted, RTECS, 1985). Drinking water standard: No MCLs, MCLGs, or DWELs have been proposed (U.S. EPA, 2000). Source: Storm water runoff, waste motor oils, improper disposal of laboratory solvent containing bromobenzene (quoted, Verschueren, 1983) Uses: Preparation of phenyl magnesium bromide used in organic synthesis; solvent for fats, waxes, and oils; motor oil additive; crystallizing solvent; chemical intermediate.