CH2CHBr

CH2CHBr is commonly known as vinyl bromide, or 1-bromoethene. Its molecular formula is C2H3Br, and its structure features a carbon–carbon double bond with one carbon bearing two hydrogens and the other bearing one hydrogen and a bromine atom (CH2=CHBr).

Vinyl bromide is a volatile, reactive vinyl halide that can exist as a gas or a colorless liquid under ordinary conditions, depending on temperature and pressure. It is soluble in many organic solvents and has significant utility as a building block in organic synthesis. Industrial routes to vinyl bromide include the addition of hydrogen bromide to acetylene under appropriate conditions and the dehydrohalogenation of more highly brominated precursors.

In synthetic chemistry, vinyl bromide serves as a versatile substrate for a range of transformations. It participates in palladium- and nickel-catalyzed cross-coupling reactions (such as Suzuki, Negishi, and related methods) to form substituted alkenes. It can undergo hydroboration-oxidation to furnish organoboron compounds, which are useful in further carbon–carbon bond-forming steps. Vinyl bromide can also participate in radical or anionic additions at the vinyl position and, under suitable conditions, may polymerize to poly(vinyl bromide), though storage inhibitors are typically used to suppress unwanted polymerization.

Safety and handling follow standard precautions for volatile halogenated alkenes. Vinyl bromide is flammable and can be irritating to the eyes, skin, and respiratory tract. It should be handled in a well-ventilated area with appropriate personal protective equipment and stored with stabilizers to prevent premature polymerization. Related compounds include vinyl chloride and vinyl fluoride.