3050. Dichloroacetic Acid

Nomenclature

CAS number: 79-43-6
Bichloracetic acid; dichlorethanoic acid; DCA.
C2H2Cl2O2; mol wt 128.94.
C 18.63%, H 1.56%, Cl 54.99%, O 24.82%.
CHCl2COOH.

Description and references

Transformation of chloral to dichloroacetic acid: Wallach, Ann. 173, 288 (1874); Frantzen, Fikentscher, ibid. 623, 68 (1959); Rosenblum et al., Chem. Ind. (London) 1960, 718. Toxicity: Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951); P. W. Stacpoole et al., N. Engl. J. Med. 300, 372 (1979); J. L. Cicmanec et al., Fundam. Appl. Toxicol. 17, 376 (1991). Mutagenicity studies: V. Herbert et al., Am. J. Clin. Nutr. 33, 1179 (1980). Use in treatment of lactic acidosis: P. W. Stacpoole et al., N. Engl. J. Med. 309, 390 (1983).

Properties

Liquid; pungent odor. d420 1.563. bp 193-194°. Apparently occurs in two cryst forms, mp 9.7° and -4°. nD22 1.4659. Corrosive. Miscible with water, alc, ether. LD50 orally in rats: 2.82 g/kg (Smyth).

Derivative

Ethyl ester.
C4H6Cl2O2; mol wt 157.00.
C 30.60%, H 3.85%, Cl 45.16%, O 20.38%.

Properties

Liquid, bp 158.3-158.7°. d420 1.282. nD20 1.4386. Slightly sol in water; miscible with alcohol, ether.

Therapeutic Category

Caustic; keratolytic; topical astringent.

Keywords

Astringent; Keratolytic