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Usage

Uses

Used in Organic Chemistry:
3-Butenylzinc bromide is used as a nucleophilic reagent for substitution and addition reactions, allowing chemists to introduce new functional groups or modify existing ones in a molecule. This property makes it a valuable tool in the synthesis of complex organic compounds.
Used in Cross-Coupling Reactions:
In the field of cross-coupling reactions, 3-butenylzinc bromide is used as a reagent in Negishi couplings. These reactions are essential for the formation of carbon-carbon bonds, which are crucial in the synthesis of various organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Pharmaceutical Industry:
3-Butenylzinc bromide plays a significant role in the pharmaceutical industry, as it aids in the synthesis of complex drug molecules. Its ability to participate in various types of chemical reactions allows for the creation of novel compounds with potential therapeutic applications.
Used in Material Science:
In the field of material science, 3-butenylzinc bromide is utilized in the development of advanced materials with specific properties. Its involvement in cross-coupling reactions enables the synthesis of novel polymers and other materials with tailored characteristics for various applications, such as electronics, energy storage, and coatings.

InChI:InChI=1/C4H7.BrH.Zn/c1-3-4-2;;/h3H,1-2,4H2;1H;/q;;+1/p-1/rC4H7BrZn/c1-2-3-4-6-5/h2H,1,3-4H2

Upstream product

• 7051-34-5 cyclopropylcarbinyl bromide 
• 7440-66-6 zinc 
• 5162-44-7 1-bromo-4-butene 

Relevant academic research and scientific papers

Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N, N-Dimethylacetamide

Monoorganozinc reagents, readily obtained from alkyl bromides, display excellent reactivity with β,β-disubstituted enones and TMSCl in the presence of Cu(I) and Cu(II) salts to synthesize a variety of cyclic functionalized β-quaternary ketones in 38-99% yields and 9:1-20:1 diastereoselectivities. The conjugate addition features a pronounced improvement in DMA using monoorganozinc bromide reagents. A simple one-pot protocol that harnesses in situ generated monoorganozinc reagents delivers comparable product yields.

The reaction of active zinc with organic bromides

The oxidative addition of highly reactive zinc to organic bromides shows a pronounced structure-reactivity dependence, in contrast to that shown by other metals. The kinetic and LFER studies suggest a mechanism in which electron transfer (ET) is the rate-determining step of the reaction. Experiments carried out with radical clocks as well as the stereochemical outcome of the reaction support the presence of radicals. The reactivity profiles suggest that the ET has an important component of inner-sphere process in the reaction with alkyl bromides. In the case of aryl halides, Hammet plots are consistent with the participation of aryl halide radical anions as intermediates. The reaction contemplated here can be ascribed as another example of radical-mediated selective reaction, and it has straightforward synthetic applications. Some synthetic work was done in this direction, to demonstrate how this structure-reactivity dependence can be used to obtain selective organozinc formation in unsymmetrical dibromides.