Chlorophenols

Title: Chlorophenols
Molecular Formula: C6H5ClO
Molecular Weight: 128.56
Percent Composition: C 56.05%, H 3.92%, Cl 27.58%, O 12.45%
Literature 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 Type: m-Chlorophenol
CAS Registry Number: 108-43-0
Additional Names: 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. Slightly sol in cold water; sol in alcohol, ether, caustic alkali solns. LD50 orally in rats: 0.57 g/kg (Deichmann).
Melting point: mp 33.5°
Boiling point: bp 214°
Index of refraction: nD40 1.5565
Density: d445 1.245; d478 1.214
Toxicity data: LD50 orally in rats: 0.57 g/kg (Deichmann)
Derivative Type: o-Chlorophenol
CAS Registry Number: 95-57-8
Additional Names: 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. Freely sol in alcohol, ether, caustic alkali solns; slightly sol in water. LD50 orally in rats: 0.67 g/kg (Deichmann).
Melting point: mp 9.3°
Boiling point: bp 175°
Index of refraction: nD25 1.5565; n 1.5473
Density: d423 1.2573
Toxicity data: LD50 orally in rats: 0.67 g/kg (Deichmann)
Derivative Type: p-Chlorophenol
CAS Registry Number: 106-48-9
Additional Names: 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. Sparingly sol in water, liquid petrolatum; very sol in alcohol, glycerin, ether, chloroform, fixed and volatile oils: U.S.P. XXI, 1467. LD50 orally in rats: 0.67 g/kg (Deichmann).
Melting point: mp 43.2-43.7°
Boiling point: bp 220°
Index of refraction: nD55 1.5419; nD40 1.5579
Density: d478 1.2238
Toxicity data: 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.
Therap-Cat: Antiseptic.
Chloropicrin Chloroprocaine Hydrochloride Chloroselenic Acid Chlorosulfonic Acid Chlorothalonil

2-Chlorophenol

A chlorophenol is any organochloride of phenol that contains one or more covalently bonded chlorine atoms. Chlorophenols are produced by electrophilic halogenation of phenol with chlorine. Most chlorophenols have a number of different isomers. Monochlorophenols have three isomers because there is only one chlorine atom that can occupy one of three ring positions on the phenol molecule; 2-chlorophenol, for example, is the isomer that has a chlorine atom in the ortho position. Pentachlorophenol, by contrast, has only one isomer because all five available ring positions on the phenol are fully chlorinated.

Chlorophenols are commonly used as pesticides, herbicides, and disinfectants.