Dichloroacetyl chloride

Chemical properties

Dichloroacetyl chloride (DCAC) is a colourless to light yellow fuming liquid with an acrid, penetrating odor. It is irritating to the eyes and mucous membranes (HSDB 2003b). DCAC is insoluble in water, but decomposes quickly to form HCl and dichloroacetic acid (t1/2 of hydrolysis of 0.0023 seconds in water at 25°C, and 0.2 seconds in 89.1:10.9 water-acetone at -20°C (Prager et al. 2001, Ugi and Beck 1961).

The Uses of Dichloroacetyl chloride

Dichloroacetyl Chloride is a reagent used in the synthesis of substituted benzothiazoles exhibiting antitumor and anticancer activity.

Definition

ChEBI: Dichloroacetyl chloride is the acyl chloride obtained by displacement of the hydroxy group of dichloroacetic acid by chloride. It has a role as a hapten. It derives from a dichloroacetic acid.

Preparation

Dichloroacetyl chloride can be synthesized by the reaction of dichloroacetic acid and chlorosulfonic acid. Or from the oxidation of trichloroethylene. Trichloroethylene and azobisisobutyronitrile (catalyst) were heated to 100°C, and oxygen was introduced to react under 0.6MPa pressure, maintaining the oil bath temperature at 110°C, and reacted for 10h, The product dichloroacetyl chloride is distilled off under normal pressure.

General Description

Dichloroacetyl chloride is a colorless liquid with a pungent odor. Flash point 151°F Boiling point 107-108°F. Vapors are irritating to the eyes and mucous membranes. Corrosive to metals and tissue.

Air & Water Reactions

Fumes in air. Decomposed by water to dichloroacetic acid and hydrochloric acid, both corrosive, with release of heat. (NIP).

Reactivity Profile

Solutions in acetone are stable for less than two hours and fresh solution should be prepared before each use (NIP). May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Safety Profile

Questionable carcinogen with experimental tumorigenic data. Moderately toxic by ingestion, inhalation, and skin contact. Corrosive to the skin, eyes, and mucous membranes. Combustible when exposed to heat or flame. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORIDES.