115055-85-1

Basic information

• Product Name: 4-BROMOBENZYLZINC BROMIDE
• Synonyms: 4-BROMOBENZYLZINC BROMIDE;4-BROMOBENZYLZINC BROMIDE, 0.5M SOLUTION IN TETRAHYDROFURAN;4-bromobenzylzinc bromide solution;4-Bromobenzylzinc bromide solution 0.5 in THF;4-BroMobenzylzinc broMide, 0.5M in THF, packaged under Argon in resealable CheMSeal^t bottles;1-Bromo-4-methylbenzene zinc complex;Bromo[(4-bromophenyl)methyl]zinc;4-BroMobenzylzinc broMide solution 0.5 M in THF
• CAS NO: 115055-85-1
• Molecular Formula: C7H6Br2Zn
• Molecular Weight: 315.32
• Product Categories: Alkyl;Organozinc Halides;Reike and Organozinc Reagents
• Mol File: 115055-85-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 183.8°C at 760 mmHg
• Flash Point: 1 °F
• Appearance: /
• Density: 1.015 g/mL at 25 °C
• Vapor Pressure: 1.04mmHg at 25°C
• Storage Temp.: 2-8°C
• Sensitive: Air Sensitive
• CAS DataBase Reference: 4-BROMOBENZYLZINC BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOBENZYLZINC BROMIDE(115055-85-1)
• EPA Substance Registry System: 4-BROMOBENZYLZINC BROMIDE(115055-85-1)

Safety Data

• Hazard Codes: F,Xn
• Statements: 14-19-22-36/38-40-36/37-11
• Safety Statements: 16-26-33-36-36/37
• RIDADR: UN 2056 3/PG 2
• WGK Germany: 1
• HazardClass: 4.3
• Hazardous Substances Data: 115055-85-1(Hazardous Substances Data)

Usage

General Description

4-Bromobenzylzinc bromide is a chemical compound consisting of a benzene ring with a bromine substituent and a zinc atom bonded to the benzyl group. It is commonly used as a reagent in organic synthesis to facilitate carbon-carbon bond formation through cross-coupling reactions. 4-BROMOBENZYLZINC BROMIDE is valued for its ability to participate in the Grignard reaction, which allows for the introduction of the benzylzinc group into various organic molecules. Its reactivity and selectivity make 4-bromobenzylzinc bromide a valuable tool for the efficient construction of complex organic molecules in academic and industrial settings.

InChI:InChI=1/C7H6Br.BrH.Zn/c1-6-2-4-7(8)5-3-6;;/h2-5H,1H2;1H;/q-1;;+2/p-1/rC7H6Br.BrZn/c1-6-2-4-7(8)5-3-6;1-2/h2-5H,1H2;/q-1;+1

Upstream product

• 589-15-1 1-bromomethyl-4-bromobenzene 
• 7440-66-6 zinc 

Downstream Products

• 1465120-34-6 (S)-ethyl 2-[(S)-(4-bromophenyl)methanesulfinamido]-3,3-dimethylbutanoate 
• 1465120-56-2 C₁₅H₂₂BrNO₃S 
• 1595262-48-8 C₁₉H₂₂Br₂O₂ 
• 19829-56-2 4,4'-dibromobibenzyl 

Relevant articles and documents

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.).

Novel preparation of N-arylmethyl-N-arylmethyleneamine N-oxides from benzylic bromides with zinc and isobutyl nitrite

Treatment of benzylic bromides with Zn and LiCl, followed by the reaction with i-butyl nitrite gave N-arylmethyl-N-arylmethyleneamine N-oxides in moderate yields. The present reaction is a novel and simple method for the preparation of nitrones from benzylic bromides, although the yields are moderate.

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.