2129. Chlorobutanol

Nomenclature

CAS number: 57-15-8
1,1,1-Trichloro-2-methyl-2-propanol; β,β,β-trichloro-tert-butyl alcohol; acetone chloroform; chlorbutol; Chloretone (Parke-Davis); Coliquifilm (Allergan); Methaform; Sedaform.
C4H7Cl3O; mol wt 177.46.
C 27.07%, H 3.98%, Cl 59.93%, O 9.02%.

Description and references

Chlorobutanol may be anhydrous or it may contain up to about one-half molecule of water. Prepn: Fishburn, Watson, J. Am. Pharm. Assoc. 28, 491 (1939); E. Bergman, US 2446453 (1948 to Polymerisable Products Ltd.); P. Riegger, H. Richtzenbain, DE 1271697 (1968 to Dynamit Nobel A.-G.), C.A. 69, 95967g (1968); M. Saljoughian, Monatsh. Chem. 114, 813 (1983). Toxicity studies: E. Impens, Arch. Int. Pharmacodyn. Ther. 8, 77 (1901).

Chemical structure

Properties

Crystals. Camphor odor and taste. A crystal of chlorobutanol placed on a water surface “dances” like a camphor crystal. Sublimes easily. The anhydrous form mp 97° (the hemihydrate mp 78°). bp760 167°; bp246 135°. Easily sol in hot water; one gram dissolves in 1 ml alcohol, 10 ml glycerol; sol in chloroform, ether, acetone, petr ether, glacial acetic acid, oils. MLD orally in dogs, rabbits (mg/kg): 238, 213 (Impens).

Derivative

Compd with chloral hydrate.

Description and references

Ref: DE 151188 (1904).

Properties

mp 65°.

Use

Plasticizer for cellulose esters and ethers. Preservative for biological fluids, hypodermic solns, and solns of alkaloids. Pharmaceutic aid (antimicrobial).

Therapeutic Category

Analgesic (dental).

Therapeutic Category (Veterinary)

Has been used as a mild sedative, antipruritic, and antiseptic.

Keywords

Analgesic (Dental)