308796-14-7

Basic information

• Product Name: PHENETHYLZINC BROMIDE
• Synonyms: PHENETHYLZINC BROMIDE;PHENETHYLZINC BROMIDE, 0.5M SOLUTION IN;phenethylzinc bromide solution;Phenethylzinc bromide solution 0.5 in THF;2-Phenylethylzinc broMide, 0.5M in THF, packaged under Argon in resealable CheMSeal^t bottles;Phenethylzinc bromide solution 0.5 M in THF;2-Phenylethylzinc bromide;Phenethylzinc bromide, 0.50 M in THF
• CAS NO: 308796-14-7
• Molecular Formula: C8H9BrZn
• Molecular Weight: 250.45
• Product Categories: Alkyl;Organozinc Halides;Reike and Organozinc Reagents;Chemical Synthesis;Organometallic Reagents;Organozinc Halides;Rieke and Organozinc Reagents
• Mol File: 308796-14-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 65 °C
• Flash Point: 1 °F
• Appearance: /
• Density: 0.965 g/mL at 25 °C
• Storage Temp.: 2-8°C
• Water Solubility: Reacts with water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: PHENETHYLZINC BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENETHYLZINC BROMIDE(308796-14-7)
• EPA Substance Registry System: PHENETHYLZINC BROMIDE(308796-14-7)

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: 308796-14-7(Hazardous Substances Data)

Usage

Description

PHENETHYLZINC BROMIDE is an organozinc compound that serves as a versatile reagent in various chemical reactions, particularly in the field of organic synthesis. It is known for its ability to form carbon-carbon bonds, making it a valuable component in the synthesis of complex organic molecules.

Uses

Used in Organic Synthesis:
PHENETHYLZINC BROMIDE is used as a reagent for the transition metal-catalyzed Negishi cross-coupling reaction. This reaction allows for the preparation of aryl or heteroaryl derivatives by reacting with organic halides or triflates via carbon-carbon bond formation. This application is crucial in the synthesis of various complex organic molecules and pharmaceutical compounds.
Used in the Synthesis of (4-phenyl-1-butyn-1-yl)benzene:
PHENETHYLZINC BROMIDE is used as a reagent in the palladium-catalyzed cross-coupling reaction to prepare (4-phenyl-1-butyn-1-yl)benzene. This specific application demonstrates the compound's utility in creating structurally diverse and complex organic molecules, which can be further utilized in various chemical and pharmaceutical applications.
Used in the Synthesis of Benzyl Substituted Thienopyrimidine Derivatives:
PHENETHYLZINC BROMIDE is also used as a reagent in the synthesis of benzyl substituted thienopyrimidine derivatives. These derivatives have potential applications in the pharmaceutical industry, particularly as therapeutic agents for various diseases. The use of PHENETHYLZINC BROMIDE in this context highlights its importance in the development of novel drug candidates.

InChI:InChI=1/C8H9.BrH.Zn/c1-2-8-6-4-3-5-7-8;;/h3-7H,1-2H2;1H;/q;;+1/p-1/rC8H9BrZn/c9-10-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 106-93-4 ethylene dibromide 
• 7440-66-6 zinc 

Downstream Products

• 73436-03-0 2-geranyl-5-(2-phenylethyl)resorcin 
• 10264-10-5 N-benzyl-3-phenylpropanamide 
• 1436688-37-7 2-(2-chlorophenyl)-7-(2-phenethyl)imidazo[4,5-c]quinolin-4(5H)-one 

Relevant articles and documents

Palladium-catalyzed secondary benzylic imidoylative reactions

Reported herein is a palladium-catalyzed secondary benzylic imidoylative Negishi reaction leveraging the sterically bulky aromatic isocyanides as the imine source. This method allows the facile access of alkyl-, (hetero)aryl-, and alkynylzinc reagents to afford various α-substituted phenylacetone products under mild acidic hydrolysis, which are ubiquitous motifs in many pharmaceuticals and biologically active compounds. The diastereoselective reduction of imine can be accomplished to provide the expedient conversion of secondary benzylic halide into α-substituted phenethylamine derivatives with high atom economy.

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.

A general strategy for the synthesis of enantiomerically pure azetidines and aziridines through nickel-catalyzed cross-coupling

Abstract In this communication, we report a straightforward synthesis of enantiomerically pure 2-alkyl azetidines. The protocol is based on a highly regioselective nickel-catalyzed cross-coupling of aliphatic organozinc reagents with an aziridine that fea