117269-72-4

Basic information

• Product Name: 3-CYANOBENZYLZINC BROMIDE
• Synonyms: 3-CYANOBENZYLZINC BROMIDE;3-CYANOBENZYLZINC BROMIDE, 0.5M SOLUTION IN TETRAHYDROFURAN;3-cyanobenzylzinc bromide solution;3-Cyanobenzylzinc bromide solution 0.5 M in THF;(3-cyanobenzyl)zinc(II) broMide;3-Cyanobenzylzinc bromide 0.5 M in Tetrahydrofuran
• CAS NO: 117269-72-4
• Molecular Formula: C₈H₆BrNZn
• Molecular Weight: 261.43
• Product Categories: Alkyl;Organozinc Halides;Reike and Organozinc Reagents
• Mol File: 117269-72-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: 1 °F
• Appearance: /
• Density: 0.966 g/mL at 25 °C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-CYANOBENZYLZINC BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANOBENZYLZINC BROMIDE(117269-72-4)
• EPA Substance Registry System: 3-CYANOBENZYLZINC BROMIDE(117269-72-4)

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
• Hazardous Substances Data: 117269-72-4(Hazardous Substances Data)

Usage

General Description

3-Cyanobenzylzinc bromide is an organozinc reagent commonly used in organic synthesis as a nucleophilic coupling agent. It is an important building block in the preparation of various pharmaceuticals, agrochemicals, and other organic compounds. This chemical is known for its high reactivity and selectivity in C-C and C-N bond formations, making it a valuable tool for the construction of complex molecular structures. 3-Cyanobenzylzinc bromide is a versatile and powerful reagent that has found widespread application in the field of organic chemistry.

InChI:InChI=1/C8H6N.BrH.Zn/c1-7-3-2-4-8(5-7)6-9;;/h2-5H,1H2;1H;/q;;+1/p-1/rC8H6BrNZn/c9-11-6-8-3-1-2-7(4-8)5-10/h1-4H,6H2

Upstream product

• 28188-41-2 m-(bromomethyl)benzonitrile 
• 7440-66-6 zinc 

Downstream Products

• 4381-01-5 1,2-bis(3-cyanophenyl)ethane 
• 1006713-43-4 3-[2-phenyl-N-(2-pyridylsulfonylamino)ethyl]benzonitrile 
• 1296846-48-4 3-[6-chloro-2-(2-chloroethenylidene)hexyl]benzonitrile 
• 1296846-45-1 3-(4-chloro-2-methylbuta-2,3-dien-1-yl)benzonitrile 
• 1296846-65-5 3-[4-(5-bromopyridin-3-yl)-2-methylbuta-2,3-dien-1-yl]benzonitrile 
• 1465120-37-9 (S)-ethyl 2-[(S)-(3-cyanophenyl)methanesulfinamido]-3,3-dimethylbutanoate 
• 1562309-89-0 (S)-ethyl 2-[(R)-(3-cyanophenyl)methanesulfinamido]-3,3-dimethylbutanoate 
• 1465120-59-5 C₁₆H₂₂N₂O₃S 
• 1471996-98-1 {(S)-6-[(R)-4-(3-cyano-benzyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester 

Relevant articles and documents

COMPOUNDS, COMPOSITIONS AND METHODS FOR HISTONE LYSINE DEMETHYLASE INHIBITION

The present disclosure relates generally to compounds and pharmaceutical compositions for the selective inhibition of histone lysine demethylase5 (KDM5), particularly KDM5B, and methods of their use in treating conditions and diseases associated with KDM5 activity.

Radical migration-addition of N-tert-butanesulfinyl imines with organozinc reagents

A novel migration-addition sequence was discovered for the reaction of enantioenriched N-tert-butanesulfinyl iminoacetate 1a with functionalized benzylzinc bromide reagents, producing tert-leucine derivatives in excellent diastereoselectivity (dr 98:2). The absolute configurations of two new chiral centers were unambiguously assigned by chemical transformations and X-ray crystallography. In addition, the regio- and diastereoselectivities of this novel reaction were both explained through the key N-sulfinamine intermediate M6 generated by the tert-butyl radical attack on the imine. Computational analysis of this reaction process, which was performed at the B3LYP/6-311++G(3df,2p)//B3LYP/6-31G-LANL2DZ level, also supported our proposed two-stage mechanism.