12Dibromopropane

1,2-dibromopropane is a halogenated hydrocarbon with the chemical formula C3H6Br2. It is typically produced by the addition of bromine to propene, giving a vicinal dibromide.

Structure and stereochemistry: The molecule consists of a three-carbon chain with bromine substituents on C-1 and C-2, giving CH2Br-CHBr-CH3. The C-2 atom is a stereocenter, so the compound exists as enantiomeric pairs (R and S) or as a racemate in typical preparations.

Preparation: Bromination of propene with Br2 across the double bond yields 1,2-dibromopropane. Alternative routes include bromination of other propyl substrates or conversion from 1-bromopropane by halogenation.

Reactions and uses: As a vicinal dibromide, it can undergo strong base–induced double dehydrohalogenation to give propyne (methylacetylene). It also serves as a versatile intermediate in organic synthesis, allowing formation of organolithium reagents via lithium–halogen exchange, or substitution to introduce further functionalities. It can be employed in the preparation of alkynes, polymers, or as a building block for chiral synthesis by resolution of its enantiomers.

Safety and handling: 1,2-dibromopropane is a toxic, lachrymatory, and potentially harmful chemical. It should be handled in a fume hood with appropriate personal protective equipment. It can release hydrogen bromide upon decomposition or reaction with bases; avoid inhalation, ingestion, or skin contact. Store in a cool, dry, well-ventilated area away from oxidizers.