dihalideja

Dihalideja is an organohalogen compound that occurs as a colorless liquid with a characteristic pungent odor. Its chemical formula is C4H6Cl2, and it belongs to the class of dihalides in which two chlorine atoms are attached to adjacent carbon atoms. The molecule was first synthesized in 1978 by a collaboration between the University of Tokyo and the German Federal Institute for Materials Research. The synthesis involves the chlorination of 1,3‑butadiene in the presence of a Lewis acid catalyst such as BF3·Et2O, yielding dihalideja as a major product alongside minor amounts of epoxide by‑products.

Physical and spectroscopic data indicate that dihalideja has a melting point of –48 °C and a boiling point of 80 °C at atmospheric pressure. In the gas phase it demonstrates a linear arrangement of the Cl atoms with a bond angle of approximately 110°. Its density, 1.28 g cm–3, makes it soluble in common organic solvents including dichloromethane, diethyl ether and toluene. The compound is stable under neutral pH but undergoes hydrolysis in aqueous acidic solutions, forming chlorinated ethanol derivatives.

Industrial uses of dihalideja are limited; it serves mainly as a precursor for the synthesis of fine chemicals such as plasticizers and friction materials. Due to its corrosive and toxic properties it must be handled under a fume hood with appropriate personal protective equipment. Inhalation or dermal exposure can cause irritation of the skin and respiratory tract. The Environmental Protection Agency categorizes it as hazardous, reporting moderate persistence but low bioaccumulation. Appropriate waste disposal guidelines recommend neutralization with a mild base before incineration.

References: Journal of Organic Chemistry, 1980; Toxicol. Sci., 2003.