131379-17-4

Basic information

• Product Name: 2-CYANOPHENYLZINC BROMIDE
• Synonyms: 2-CYANOPHENYLZINC BROMIDE;2-CYANOPHENYLZINC BROMIDE, 0.5M SOLUTION IN TETRAHYDROFURAN;2-cyanophenylzinc bromide solution;(2-Cyanophenyl)bromozinc;(o-Cyanophenyl)bromozinc;2-(Bromozincio)benzonitrile;Bromo(2-cyanophenyl) zinc;2-Cyanophenylzinc bromide solution 0.5 in THF
• CAS NO: 131379-17-4
• Molecular Formula: C₇H₄BrNZn
• Molecular Weight: 247.41
• Product Categories: Alkyl;Organozinc Halides;Reike and Organozinc Reagents
• Mol File: 131379-17-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: 1 °F
• Appearance: /
• Density: 0.979 g/mL at 25 °C
• Vapor Pressure: 0.524mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-CYANOPHENYLZINC BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CYANOPHENYLZINC BROMIDE(131379-17-4)
• EPA Substance Registry System: 2-CYANOPHENYLZINC BROMIDE(131379-17-4)

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 3399 4.3/PG 2
• WGK Germany: 1
• Hazardous Substances Data: 131379-17-4(Hazardous Substances Data)

Usage

General Description

2-Cyanophenylzinc bromide is a chemical compound that is primarily used as a building block in organic synthesis. It is a zinc organometallic reagent that is often utilized in the formation of carbon-carbon bonds through cross-coupling reactions. 2-CYANOPHENYLZINC BROMIDE is known for its ability to undergo reactions with a wide variety of electrophiles, making it a versatile tool in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique reactivity and selectivity make it a valuable reagent in organic chemistry, particularly for the construction of complex molecular structures. Additionally, 2-Cyanophenylzinc bromide is known for its high stability in storage and handling, making it a reliable choice for use in laboratory-scale and industrial-scale reactions.

InChI:InChI=1/C7H4N.BrH.Zn/c8-6-7-4-2-1-3-5-7;;/h1-4H;1H;/q-1;;+2/p-1/rC7H4N.BrZn/c8-6-7-4-2-1-3-5-7;1-2/h1-4H;/q-1;+1

Upstream product

• 2042-37-7 o-cyanobromobenzene 
• 7699-45-8 zinc dibromide 
• 7440-66-6 zinc 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 868286-71-9 3-((2R)-5-(2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(2-(aminomethyl)phenyl)-N-methyl-N-(methylsulfonyl)benzenamine 
• 868286-43-5 5-(5-{(1R)-1-[(tert-butoxycarbonyl)amino]-1-methyl-2-phenylethyl}-1,3,4-oxadiazol-2-yl)-2'-cyanobiphenyl-3-carboxylic acid 
• 868286-44-6 methyl 5-(5-{(1R)-1-[(tert-butoxycarbonyl)amino]-1-methyl-2-phenylethyl}-1,3,4-oxadiazol-2-yl)-2'-cyanobiphenyl-3-carboxylate 
• 887970-28-7 C₃₉H₃₉N₃O₅ 
• 868286-70-8 3-((2R)-5-(2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(2-(carbonitrile)phenyl)-N-methyl-N-(methylsulfonyl)benzenamine 
• 135689-93-9 4-(2-Cyanophenyl)benzaldehyde 

Relevant articles and documents

Scalability of microwave-assisted organic synthesis. From single-mode to multimode parallel batch reactors

The direct scalability of microwave-assisted organic synthesis (MAOS) in a prototype laboratory-scale multimode microwave batch reactor is investigated. Several different organic reactions have been scaled-up typically from 1 mmol to 100 mmol scale. The transformations include multicomponent chemistries (Biginelli dihydropyrimidine and Kindler thioamide synthesis), transition metal-catalyzed carbon - carbon cross-coupling protocols (Heck and Negishi reactions), solid-phase organic synthesis, and Diels - Alder cycloaddition reactions using gaseous reagents in prepressurized reaction vessels. A range of different solvents (high and low microwave absorbing), Pd catalysts (homogeneous and heterogeneous), and varying reaction times and temperatures have been explored in these investigations. In all cases, it was possible to achieve similar isolated product yields on going from a small scale (ca. 5 mL processing volume) to a larger scale (max 500 mL volume) without changing the previously optimized reaction conditions (direct scalability). The prototype, benchtop multimode microwave reactor used in the present study allows parallel processing in either quartz or PTFE-TFM vessels with maximum operating limits of 300°C and 80 bar of pressure. The system features magnetic stirring in all vessels, complete on-line monitoring of temperature, pressure and microwave power, and the ability to maintain inert or reactive gas atmosphere.

Microwave-assisted Negishi and Kumada cross-coupling reactions of aryl chlorides

Rapid Pd or Ni-catalyzed microwave-accelerated Negishi and Kumada cross-coupling reactions of aryl chlorides in solution and on solid phase are reported.

New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust

A new chemical method for the preparation of arylzinc intermediates is described in acetonitrile, on the basis of the activation of aryl bromides by low-valent cobalt species arising from the reduction of cobalt halide by zinc dust. This procedure allows for the synthesis of a variety of functionalized aryl- and thienylzinc species in good to excellent yields. The versatility and the simplicity of that original method represent an alternative to most known procedures.