Dichloroacetic acid methyl ester

Chemical Properties

clear colorless liquid

Uses

Organic intermediate.

Uses

Dichloroacetic Acid Methyl Ester is used in the preparation of telechelics and block copolymers through living radical polymerization.

Uses

Methyl dichloroacetate may be used:

• in the diastereoselctive synthesis of bicyclic chlorocyclopropane
• as difunctional initiator during atom transfer radical polymerization of methyl or n-butyl acrylate
• as reagent during CrCl₂-induced olefination of aldehydes

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 5307, 1968 DOI: 10.1021/ja01021a065
The Journal of Organic Chemistry, 28, p. 1133, 1963

General Description

A colorless liquid with an ethereal odor. Combustible. Flash point 176°F. Corrosive to metals and tissue. Used to make other chemicals.

Air & Water Reactions

Decomposed by water to dichloroacetic acid, a corrosive material with evolution of heat [USCG, 1999].

Reactivity Profile

Dichloroacetic acid methyl ester produces toxic fumes of phosgene and HCl when heated [USCG, 1999].

Hazard

Strong irritant to tissue. Forms corrosiveproducts on hydrolysis, keep dry.

Health Hazard

Extremely destructive to the eyes, nose, throat, and upper respiratory tract. May be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.

Fire Hazard

Special Hazards of Combustion Products: Produces toxic fumes of phosgene and HCl.

Safety Profile

Poisonous irritant to the skin, eyes, and mucous membranes. Hydrolyzes upon contact with moisture to form a product corrosive to tissue. See also DICHLOROACETIC ACID and ESTERS. Dangerous; when heated to decomposition it emits hghly toxic fumes of phosgene and Cl-.