1542. tert-Butyl Alcohol

Nomenclature

CAS number: 75-65-0
2-Methyl-2-propanol; trimethyl carbinol; tert-butanol.
C4H10O; mol wt 74.12.
C 64.82%, H 13.60%, O 21.59%.

Description and references

Prepd from acetyl chloride and dimethylzinc: Butlerow, Ann. 144, 1 (1867). Manuf by catalytic hydration of isobutylene: Kreps, Nachod, US 2477380 (1949 to Atlantic Refining); Serniuk, Vanderbilt, US 2534304 (1950 to Standard Oil); by reduction of tert-butyl hydroperoxide: Lorand, US 2484841 (1949 to Hercules Powder); De Jong, US 2853532 (1958 to Shell). Purification: Biddiscombe et al., J. Chem. Soc. 1963, 1954. Physical properties: eidem, ibid.; Dreisbach, Martin, Ind. Eng. Chem. 41, 2875 (1949). Toxicity: Schaffarzick, Brown, Science 116, 663 (1952).

Chemical structure

Properties

Crystals, camphor-like odor, mp 25.6°. At 99.69 mol-% purity, bp 82.41°. mp 25.7°. d420 0.78581, d425 0.78086, d425 (calcd) 0.78080; nD20 1.38468, nD25 1.38231. Flash pt, closed cup: 52°F (11.1°C). Sol in water. Miscible with alcohol, ether. LD50 orally in rats: 3.5 g/kg (Schaffarzick, Brown).

Caution

Potential symptoms of overexposure are drowsiness, narcosis; irritation of skin, eyes, nose, throat. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 40.

Use

Denaturant for ethanol, mfg flotation agents, flavors, perfumes; as organic solvent; in paint removers. Octane booster in gasoline.