9627. Trichloroacetic Acid

Nomenclature

CAS number: 76-03-9
2,2,2-Trichloroacetic acid; TCA.
C2HCl3O2; mol wt 163.39.
C 14.70%, H 0.62%, Cl 65.10%, O 19.58%.
CCl3COOH.

Description and references

Prepd by oxidation of chloral hydrate with nitric acid: Parkes, Hollingshead, Chem. Ind. (London) 1954, 222. Manuf by chlorination of acetic acid: Eaker, US 2832803 (1958 to Monsanto). Toxicity study: G. W. Bailey, J. L. White, Residue Rev. 10, 97 (1965).

Properties

Very deliquesc crystals; slight characteristic odor. d461 1.629; mp 57-58°; bp 196-197°. Very sol in water, alcohol, ether; dec by heating with caustic alkalies into chloroform and alkali carbonate. pKa ≈0.7. pH of 0.1 molar aq soln 1.2. Corrosive. Keep tightly closed in a cool place. Storage of trichloroacetic acid solns in water of less than 30% strength is not recommended. Decompn products are chloroform, hydrochloric acid, carbon dioxide and carbon monoxide. LD50 orally in rats: 5000 mg/kg (Bailey, White).

Derivative

Ethyl ester.

Nomenclature

CAS number: 515-84-4
Ethyl trichloroacetate.
C4H5Cl3O2; mol wt 191.44.
C 25.10%, H 2.63%, Cl 55.56%, O 16.71%.

Properties

Clear liq; odor resembling menthol. d420 1.383. bp 168°. nD20 1.4507. Insol in water. Misc with alcohol, ether.

Derivative

Sodium salt.

Nomenclature

CAS number: 650-51-1
Sodium trichloroacetate; Konesta (Akzo); Varitox (M & B).
C2Cl3NaO2; mol wt 185.37.
C 12.96%, Cl 57.38%, Na 12.40%, O 17.26%.

Properties

Yellow deliquesc powder, mp >300°. Soly in water at 25°: 1.2 kg/l. Sol in ethanol.

Caution

Potential symptoms of overexposure are irritation of eyes, skin, nose, throat, respiratory system; cough, dyspnea, delayed pulmonary edema; eye and skin burns; dermatitis; salivation, vomiting, diarrhea. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 314.

Use

As a decalcifier and fixative in microscopy; also as a precipitant of protein, esp in albumin detection. As herbicide.

Therapeutic Category

Caustic.

Therapeutic Category (Veterinary)

Caustic, vesicant.