117269-72-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Cyanobenzylzinc bromide is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its high reactivity and selectivity in bond formations enable the creation of complex molecular structures, which are essential for developing new and effective drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 3-Cyanobenzylzinc bromide is utilized as a building block for the synthesis of various agrochemicals. Its ability to form C-C and C-N bonds allows for the development of innovative and efficient agrochemical products.
Used in Organic Chemistry Research:
3-Cyanobenzylzinc bromide is employed as a reagent in organic chemistry research for the construction of complex molecular structures. Its versatility and powerful reactivity make it an indispensable tool for chemists working on the synthesis of novel organic compounds and the development of new synthetic methods.
Used in the Synthesis of Organic Compounds:
3-Cyanobenzylzinc bromide is used as a nucleophilic coupling agent in the synthesis of various organic compounds. Its high reactivity and selectivity in bond formations facilitate the creation of complex molecular structures, which are crucial for the development of new materials and the advancement 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

• 55984-93-5 2-methyl-1,4-dicyanobenzene 
• 1006713-43-4 3-[2-phenyl-N-(2-pyridylsulfonylamino)ethyl]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 
• 1365530-20-6 3-(2-amino-2-(5-chloropyridin-2-yl)-2-(3-fluoro-5-(trifluoromethyl)phenyl)ethyl)benzonitrile 
• 1296846-65-5 3-[4-(5-bromopyridin-3-yl)-2-methylbuta-2,3-dien-1-yl]benzonitrile 
• 1296846-45-1 3-(4-chloro-2-methylbuta-2,3-dien-1-yl)benzonitrile 

Relevant academic research and scientific papers

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.

Palladium-catalyzed cross-coupling of benzylzinc reagents with 2-bromo-3,3,3-trifluoropropene

α-Trifluoromethyl alkenes can be used as peptide isosteres, moreover, the pre-installed vinyl group make it possible that transformation to diverse fluorine-containing unities. However, the cross-coupling of benzyl group with α-trifluoromethyl alkenes has yet to be developed. In this report, we describe a general method for the cross-coupling of benzylzinc reagents with 2-bromo-3,3,3-trifluoropropene (BTP) to afford diverse α-trifluoromethylalkene derivatives by using Pd(TFA)2 as catalyst. This method takes advantage of cheap industrial available fluorine building blocks and easily prepared benzylzinc reagents to generate α-trifluoromethylalkene derivatives, which features with mild reaction conditions, wide substrate scope and feasibility of product transformations.

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.