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

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

Uses

Used in Organic Synthesis:
4-Bromobenzylzinc bromide is used as a reagent for facilitating carbon-carbon bond formation through cross-coupling reactions. Its ability to participate in the Grignard reaction allows for the introduction of the benzylzinc group into various organic molecules, enhancing the synthesis of complex organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-bromobenzylzinc bromide is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its reactivity and selectivity contribute to the development of new drugs with improved efficacy and reduced side effects.
Used in Chemical Research:
4-Bromobenzylzinc bromide is utilized as a research tool in academic settings to explore new synthetic pathways and develop innovative methods for the construction of complex organic molecules. Its unique properties enable chemists to study the mechanisms of cross-coupling reactions and optimize reaction conditions for improved yields and selectivity.
Used in Material Science:
In the field of material science, 4-bromobenzylzinc bromide is employed in the synthesis of advanced materials with specific properties, such as organic semiconductors, polymers, and catalysts. Its ability to form carbon-carbon bonds contributes to the development of materials with tailored electronic, optical, and catalytic properties for various applications.

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 
• 1312565-66-4 tert-butyl 2-(4-bromobenzyl)pyrrolidine-1-carboxylate 
• 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.).

Formation of quaternary carbons through cobalt-catalyzed C(sp3)-C(sp3) Negishi cross-coupling

Formation of all-carbon-substituted quaternary carbons is a key challenge in organic and medicinal chemistry. We report a cobalt-catalyzed C(sp3)-C(sp3) cross-coupling that allows for the introduction of benzyl, heteroarylmethylzinc and allyl groups to halo-carbonyl substrates. The cross-coupling reaction is selective for C(sp3)-over C(sp2)-halides, in contrast to most used catalytic metals, and allows access to novel scaffolds of pharmaceutical interest. NMR mechanistic studies suggest the presence of Co(0) complexes as catalytic species. This journal is

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.

o-Nitrobenzyl photoremovable groups with fluorescence uncaging reporting properties

o-Nitrobenzyl (o-NB) derivatives are the most widely applied photoremovable groups for the study of dynamic biological processes. By introducing different substituents to the benzylic position we were able to generate a fluorescence signal upon irradiatio

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.

Reactions of organozinc reagents with potassium bromodifluoroacetate

A practical method for the synthesis of gem-difluorinated compounds from organozinc reagents is described. Potassium bromodifluoroacetate serves as a source of CF2-fragment, which is inserted into carbonzinc bond of organozinc reagents. The intermediate difluorinated organozinc species can be protonated, brominated or coupled with allylic electrophiles.

The synthesis of 1,2-diarylindenes via DDQ-mediated dehydrogenative intramolecular cyclization

A direct DDQ-mediated dehydrogenative intramolecular cyclization of (Z)-1,2,3-triaryl substituted propylenes promoted by Cu(OAc)2 was developed, providing 1,2-diarylindene derivatives in moderate to good yields (up to 92%) under mild conditions

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.