135579-87-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Cyanobenzylzinc bromide is used as a key reagent for the synthesis of biologically active compounds, contributing to the development of new drugs with potential therapeutic applications. Its high selectivity and mild reaction conditions facilitate the construction of complex organic molecules, which are essential for creating innovative pharmaceutical agents.
Used in Agrochemical Industry:
In the agrochemical industry, 4-cyanobenzylzinc bromide serves as a crucial intermediate in the synthesis of various agrochemicals, including pesticides and herbicides. Its ability to participate in a wide range of reactions allows for the creation of novel compounds with improved efficacy and selectivity in controlling pests and weeds.
Used in Organic Synthesis:
4-Cyanobenzylzinc bromide is used as a nucleophile in organic synthesis for carbon-carbon bond formation. Its versatility in performing Grignard-type reactions, addition reactions to unsaturated compounds, and other transformations makes it an indispensable tool for chemists working on the development of new organic compounds with diverse applications.
Used in Academic Research:
In academic research, 4-cyanobenzylzinc bromide is utilized as a reagent to explore new reaction pathways and mechanisms, as well as to study the properties of organozinc compounds. Its unique characteristics, such as high selectivity and mild reaction conditions, provide researchers with valuable insights into the field of organic chemistry and contribute to the advancement of scientific knowledge.

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

• 1943-88-0 2,4-dicyanotoluene 
• 135579-92-9 2,3-Di(p-cyanobenzyl)-1,3-butadiene 
• 619334-81-5 6-[5-(4-cyanobenzyl)furan-2-yl]nicotinonitrile 
• 1422039-01-7 4-(2,2-difluoro-2-iodoethyl)benzonitrile 
• 62044-11-5 4-[2-(naphthalen-1-yl)-2-oxoethyl]benzonitrile 
• 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 
• 1465120-38-0 (S)-ethyl 2-[(S)-(4-cyanophenyl)methanesulfinamido]-3,3-dimethylbutanoate 
• 1465120-61-9 C₁₆H₂₂N₂O₃S 

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.

C(sp3)?C(sp3) Bond Formation via Electrochemical Alkoxylation and Subsequent Lewis Acid Promoted Reactions

A two-step transition metal-free methodology for the C(sp3)?C(sp3) functionalisation of saturated N-heterocyclic systems is disclosed. First, aminal derivatives are generated through the anodic oxidation of readily accessible carboxylic acids. Then, in the presence of BF3 ? OEt2, iminium ions are unmasked and rapidly alkylated by organozinc reagents under flow conditions. Secondary, tertiary and quaternary carbon centers have been successfully assembled using this methodology. Such an approach is especially relevant to drug discovery since it increases C(sp3)-functionalities rapidly within a molecular framework. As proof of concept, our methodology was applied to derivatization of peptides and an API. (Figure presented.).

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.

Efficient and General Aerobic Oxidative Cross-Coupling of THIQs with Organozinc Reagents Catalyzed by CuCl2: Proof of a Radical Intermediate

A general new method for the highly concise synthesis of C-1-alkylated tetrahydroisoquinolines (THIQ) is reported. The CuCl2-catalyzed procedure is based on a coupling of nonfunctionalized THIQs with organozinc reagents under aerobic conditions. It proceeds in high yields and is broadly applicable to a wide range of substrates. It relies on a regioselective sp3 C-H bond activation allowing for an sp3-sp3 bond union under mild reaction conditions in a rapid and effective manner. Mechanistically it involves an iminium ion intermediate that is formed via an organic radical involving a single-electron-transfer process. For the first time for this type of reaction a radical intermediate has been proven by EPR spectroscopy.

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.