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.

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