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Usage

Uses

Used in Pharmaceutical Industry:
4-CYANOBUTYLZINC BROMIDE is used as a reactant for the synthesis of complex organic molecules, particularly in the development of pharmaceutical compounds. Its ability to form carbon-carbon bonds through Negishi cross-coupling reactions allows for the creation of diverse molecular structures with potential therapeutic applications.
Used in Chemical Synthesis:
4-CYANOBUTYLZINC BROMIDE is used as a reactant in the preparation of specific organic compounds, such as 5-(3-Thienyl)pentanenitrile and α-Cyanobutyl vinylphosphonates. The compound is utilized in reactions with 3-bromothiophene in the presence of a nickel catalyst to produce 5-(3-Thienyl)pentanenitrile, and in palladium-catalyzed Negishi coupling vinylation reactions with α-(pseudo)halo vinylphosphonates to synthesize α-Cyanobutyl vinylphosphonates.
Used in Material Science:
4-CYANOBUTYLZINC BROMIDE can be employed as a building block in the development of novel materials with specific properties. Its role in forming carbon-carbon bonds through Negishi cross-coupling reactions enables the creation of new materials with tailored characteristics for various applications, such as electronics, coatings, and adhesives.

InChI:InChI=1/C5H8N.BrH.Zn/c1-2-3-4-5-6;;/h1-4H2;1H;/q-1;;+2/p-1/rC5H8N.BrZn/c1-2-3-4-5-6;1-2/h1-4H2;/q-1;+1

Upstream product

• 5414-21-1 5-bromopentan-1-nitrile 
• 106-93-4 ethylene dibromide 
• 7440-66-6 zinc 

Downstream Products

• 1439400-48-2 N-(6-(4-cyanobutyl)pyridazin-3-yl)-2-(3-(trifluoromethoxy)phenyl)acetamide 

Relevant academic research and scientific papers

Palladium-catalyzed secondary benzylic imidoylative reactions

Reported herein is a palladium-catalyzed secondary benzylic imidoylative Negishi reaction leveraging the sterically bulky aromatic isocyanides as the imine source. This method allows the facile access of alkyl-, (hetero)aryl-, and alkynylzinc reagents to afford various α-substituted phenylacetone products under mild acidic hydrolysis, which are ubiquitous motifs in many pharmaceuticals and biologically active compounds. The diastereoselective reduction of imine can be accomplished to provide the expedient conversion of secondary benzylic halide into α-substituted phenethylamine derivatives with high atom economy.

Continuous flow Negishi cross-couplings employing silica-supported: Pd-PEPPSI - IPr precatalyst

The synthesis of a triethoxysilyl functionalised Pd-PEPPSI-IPr complex prepared via azide-alkyne cycloaddition is described. The complex was immobilised onto silica gel and applied as a heterogeneous catalyst in the Negishi reaction. The catalyst was active in both batch and continuous flow operation and was particularly effective for the coupling of heteroaryl chlorides. Long-term continuous flow experiments demonstrated good catalyst activity over fifteen hours.

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.