2154. Chlorophenols
C6H5ClO; mol wt 128.56.
C 56.05%, H 3.92%, Cl 27.58%, O 12.45%.
Description and references
Prepn of o-form: Holleman, Rinkes, Rec. Trav. Chim. 30, 48 (1911); Huston, Neely, J. Am. Chem. Soc. 57, 2176 (1935). cis-trans equilibria in o-halophenols: Baker, ibid. 80, 3598 (1958). Prepn of p-form: Crawford, Willson, US 1910679 (1927 to Monsanto); Neu, Ber. 72, 1505 (1939); Hodgson, Norris, J. Chem. Soc. 1949, Suppl. 1, S181. Manuf: Britton, Keil, US 2725402 (1955 to Dow). Prepn of m-form: Acheson, Taylor, J. Chem. Soc. 1956, 4727. Manuf: Stoesser, Gentry; Barnard, Meyer, US 2835707 and US 2852567 (both 1958 to Dow). Toxicity data: Deichmann, Fed. Proc. 2, 76 (1943). Review of toxicology and human exposure: Toxicological Profile for Chlorophenols (PB99-166639, 1999) 260 pp.
Derivative
m-Chlorophenol.Nomenclature
CAS number: 108-43-0
3-Chlorophenol. Properties
Needles, mp 33.5°. bp 214°. d445 1.245, d478 1.214. nD40 1.5565. Strong medicinal taste and odor. Dipole moment in benzene, 2.10D. Poisonous. Slightly sol in cold water; sol in alcohol, ether, caustic alkali solns. LD50 orally in rats: 0.57 g/kg (Deichmann).Derivative
o-Chlorophenol.Nomenclature
CAS number: 95-57-8
2-Chlorophenol. Properties
Liquid, bp 175°. mp 9.3°. d423 1.2573. nD25 1.5565; n 1.5473. Strong medicinal taste and odor. Dipole moment in benzene, 1.33D. Poisonous. Freely sol in alcohol, ether, caustic alkali solns; slightly sol in water. LD50 orally in rats: 0.67 g/kg (Deichmann).Derivative
p-Chlorophenol.Nomenclature
CAS number: 106-48-9
4-Chlorophenol. Properties
Crystals with characteristic phenolic odor, mp 43.2-43.7°. bp 220°. d478 1.2238. nD55 1.5419; nD40 1.5579. Dipole moment in benzene, 2.22D. Poisonous. Sparingly sol in water, liquid petrolatum; very sol in alcohol, glycerin, ether, chloroform, fixed and volatile oils: USP XXI, 1467. LD50 orally in rats: 0.67 g/kg (Deichmann).Caution
Potential symptoms of overexposure are tremors, convulsions, dyspnea, coma. Direct contact may cause skin irritation. See: Patty's Industrial Hygiene and Toxicology Vol. 2A, G. D. Clayton, F. E. Clayton, Eds. (Wiley-Interscience, New York, 3rd ed., 1981) pp 2612-2615.Use
Biocide; disinfectant for home, hospital and farm.Therapeutic Category
Antiseptic.