1112. Benzoyl Chloride

Nomenclature

CAS number: 98-88-4
Benzenecarbonyl chloride.
C7H5ClO; mol wt 140.57.
C 59.81%, H 3.59%, Cl 25.22%, O 11.38%.

Description and references

Prepd by partial hydrolysis of benzotrichloride: Davies, Dick, J. Chem. Soc. 1932, 2808; by chlorination of benzaldehyde: W"ohler, Ann. 3, 262 (1832). Lab prepn from benzoic acid and thionyl chloride: A. I. Vogel, Practical Organic Chemistry (Longmans, London, 3rd ed., 1959) p 792; Gattermann-Wieland, Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961) p 112. Microwave structural study: M. Onda et al., J. Mol. Struct. 162, 183 (1987). Derivatization of polyamines for HPLC determn: Y.-H. Mei, J. Liq. Chromatogr. 17, 2413 (1994).

Chemical structure

Properties

Liquid. Penetrating odor. d425 1.2070. mp -1.0°. bp760 197.2°; bp35 100°; bp15 82.3°; bp9 71°; bp3 49°. nD20 1.55369. Dipole moment 3.28. Flash pt 88°C (190.4°F). Parachor 289.8. Corrosive. Dec by water and alc. Miscible with ether, benzene, carbon disulfide, oils.

Caution

Lacrimator. Potential symptoms of overexposure may include irritation and burns of skin, eyes, mucous membranes, and respiratory tract.

Use

For acylation, i.e., introduction of the benzoyl group into alcohols, phenols, and amines (Schotten-Baumann reaction); in the manuf of benzoyl peroxide and of dye intermediates. In organic analysis for making benzoyl derivatives for identification purposes.