135579-87-2

Basic information

• Product Name: 4-CYANOBENZYLZINC BROMIDE
• Synonyms: 4-CYANOBENZYLZINC BROMIDE;4-CYANOBENZYLZINC BROMIDE, 0.5M SOLUTION IN TETRAHYDROFURAN;4-cyanobenzylzinc bromide solution;4-Cyanobenzylzinc bromide solution 0.5 in THF;4-Cyanobenzylzinc bromide solution 0.5M in THF
• CAS NO: 135579-87-2
• Molecular Formula: C₈H₆BrNZn
• Molecular Weight: 261.43
• Product Categories: Alkyl;Organozinc Halides;Reike and Organozinc Reagents
• Mol File: 135579-87-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: 1 °F
• Appearance: /
• Density: 0.956 g/mL at 25 °C
• Vapor Pressure: 0.126mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-CYANOBENZYLZINC BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANOBENZYLZINC BROMIDE(135579-87-2)
• EPA Substance Registry System: 4-CYANOBENZYLZINC BROMIDE(135579-87-2)

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: 135579-87-2(Hazardous Substances Data)

Usage

General Description

4-Cyanobenzylzinc bromide is an organozinc compound that is typically used in organic synthesis as a nucleophile for carbon-carbon bond formation. It is a versatile reagent known for its ability to effectively perform a wide range of reactions, including Grignard-type reactions, addition reactions to unsaturated compounds, and various other transformations. 4-CYANOBENZYLZINC BROMIDE is particularly useful in the construction of complex organic molecules and is frequently employed in the pharmaceutical and agrochemical industries for the synthesis of biologically active compounds. Additionally, 4-cyanobenzylzinc bromide is known for its high selectivity and mild reaction conditions, making it a valuable tool for chemists seeking to efficiently produce a diverse array of organic compounds.

InChI:InChI=1/C8H6N.BrH.Zn/c1-7-2-4-8(6-9)5-3-7;;/h2-5H,1H2;1H;/q-1;;+2/p-1/rC8H6N.BrZn/c1-7-2-4-8(6-9)5-3-7;1-2/h2-5H,1H2;/q-1;+1

Upstream product

• 17201-43-3 4-cyanobenzyl bromide 
• 7440-66-6 zinc 

Downstream Products

• 1422039-01-7 4-(2,2-difluoro-2-iodoethyl)benzonitrile 
• 1465120-38-0 (S)-ethyl 2-[(S)-(4-cyanophenyl)methanesulfinamido]-3,3-dimethylbutanoate 
• 1465120-61-9 C₁₆H₂₂N₂O₃S 
• 1471996-83-4 {(S)-6-[(R)-4-(4-cyano-benzyl)-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester 
• 62044-11-5 4-[2-(naphthalen-1-yl)-2-oxoethyl]benzonitrile 
• 62043-70-3 4-(3-chloro-2-oxopropyl)benzonitrile 
• 619334-81-5 6-[5-(4-cyanobenzyl)furan-2-yl]nicotinonitrile 

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.

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.