36333-41-2

Usage

Type of compound

Highly reactive diacetylene derivative

Structure

Two bromine atoms attached to a carbon-carbon triple bond

Common use

Precursor in organic synthesis

Chemical properties

Unique due to bromine atoms and triple bond

Application

Preparation of conjugated polymers and functional materials

Polymerization

Ability to form long chains of carbon atoms

Field of study

Materials science

Potential applications

Electronic and optoelectronic devices

Reactivity

High, which can pose hazards

Value

Important compound in organic chemistry and materials research

Upstream product

• 460-12-8 Butadiyne 
• 4526-07-2 1,4-bis(trimethylsilyl)-1,3-butadiyne 

Downstream Products

• 53978-00-0 hexabromo-1,3-butadiene 

Relevant academic research and scientific papers

Synthesis of the stable ordered conjugated polymer poly(dibromodiacetylene) from an explosive monomer

Dibromobutadiyne is an extremely unstable compound that explodes at room temperature, even under inert atmosphere. This instability has limited the studies of dibromobutadiyne almost entirely to spectroscopic characterization. Here we report an approach t

Tetrabromobutatriene: Completing the perhalocumulene series

Tetrabromobutatriene, C4Br4, can be prepared directly from dibromobutadiyne by reaction with Br2 at -25°C in concentrated hexanes solution. The cumulene precipitates out of the reaction mixture as a yellow powder. Under palladium-catalyzed coupling conditions, C4Br4 can undergo allylic rearrangement, giving a mixture of products, including some with butenyne backbones. However, in furan solution, C4Br4 reacts cleanly at its central double bond to give the furan Diels-Alder adduct. Under Suzuki conditions, this adduct reacts at the furan double bond rather than at bromide.