312624-28-5

Basic information

• Product Name: 6-CYANOHEXYLZINC BROMIDE
• Synonyms: 6-CYANOHEXYLZINC BROMIDE;6-CYANOHEXYLZINC BROMIDE, 0.5M SOLUTIONI N TETRAHYDROFURAN;6-cyanohexylzinc bromide solution;6-Cyanohexylzinc bromide solution 0.5 in THF;6-Cyanohexylzinc broMide, 0.5M in THF, packaged under Argon in resealable CheMSeal^t bottles;6-Cyanohexylzinc bromide, 0.5M in THF, packaged under Argon in resealable ChemSeal™6-Cyanohexylzinc bromide, Packaged under Argon in resealable ChemSeal? bottles;6-Cyanohexylzinc bromide solution 0.5M in THF
• CAS NO: 312624-28-5
• Molecular Formula: C7H12BrNZn
• Molecular Weight: 255.47
• Product Categories: Alkyl;Organozinc Halides;Reike and Organozinc Reagents
• Mol File: 312624-28-5.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: 1 °F
• Appearance: /
• Density: 0.944 g/mL at 25 °C
• Vapor Pressure: 0.679mmHg at 25°C
• Storage Temp.: 2-8°C
• Sensitive: Air Sensitive
• CAS DataBase Reference: 6-CYANOHEXYLZINC BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CYANOHEXYLZINC BROMIDE(312624-28-5)
• EPA Substance Registry System: 6-CYANOHEXYLZINC BROMIDE(312624-28-5)

Safety Data

• Hazard Codes: F,Xn
• Statements: 19-22-36/38-40-36/37-14-11
• Safety Statements: 16-26-33-36-36/37
• RIDADR: UN 2056 3/PG 2
• WGK Germany: 1
• HazardClass: 4.3
• Hazardous Substances Data: 312624-28-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
6-CYANOHEXYLZINC BROMIDE is used as a reactant in palladium-catalyzed Negishi cross-coupling reactions for the construction of carbon-carbon bonds. This process is crucial for the synthesis of complex organic molecules and the development of new pharmaceuticals and materials.
Used in Pharmaceutical Industry:
6-CYANOHEXYLZINC BROMIDE is used as a reactant to synthesize cyanohexyl substituted aryl derivatives through palladium-catalyzed coupling reactions with aryl bromides. These derivatives are valuable intermediates in the development of pharmaceutical compounds with potential therapeutic applications.
Used in Chemical Intermediates:
6-CYANOHEXYLZINC BROMIDE is used as a reactant in the synthesis of Methyl 5-(6-cyanohexyl)-3-methylfuran-2-carboxylate, a key intermediate in the preparation of cyclic furfuryl ether via Wittig rearrangement. This intermediate is essential for the production of various chemical compounds and materials with diverse applications.

InChI:InChI=1/C7H12N.BrH.Zn/c1-2-3-4-5-6-7-8;;/h1-6H2;1H;/q-1;;+2/p-1/rC7H12N.BrZn/c1-2-3-4-5-6-7-8;1-2/h1-6H2;/q-1;+1

Upstream product

• 20965-27-9 7-bromo-heptanonitrile 
• 7440-66-6 zinc 

Downstream Products

• 629-08-3 heptanenitrile 

Relevant articles and documents

Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling

A form independent activation of zinc, concomitant generation of organozinc species and engagement in a Negishi cross-coupling reaction via mechanochemical methods is reported. The reported method exhibits a broad substrate scope for both C(sp3)–C(sp2) and C(sp2)–C(sp2) couplings and is tolerant to many important functional groups. The method may offer broad reaching opportunities for the in situ generation organometallic compounds from base metals and their concomitant engagement in synthetic reactions via mechanochemical methods.

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.