2139. 2-Chloroethyl Vinyl Ether

Nomenclature

CAS number: 110-75-8
(2-Chloroethoxy)ethene.
C4H7ClO; mol wt 106.55.
C 45.09%, H 6.62%, Cl 33.27%, O 15.02%.

Description and references

Prepd by the action of solid NaOH + triethanolamine upon β,β′-dichlorodiethyl ether: Chitwood, Perkins, US 2104717 (1938 to Carbide and Carbon Chem.); cf. Cretcher et al., J. Am. Chem. Soc. 47, 1175 (1926). Toxicity study: Smyth et al., J. Ind. Hyg. Toxicol. 31, 60 (1949).

Chemical structure

Properties

Liquid. d1515 1.0525. bp740 109°. Quite stable to NaOH solns. Even dil acids produce hydrolysis to acetaldehyde and ethylene chlorohydrin [2-chloroethanol]. LD50 orally in rats: 250 mg/kg (Smyth).

Use

Mfg anesthetics, sedatives, cellulose ethers.