Bromozinc(1+);(6-methylidenecyclohexa-2,4-dien-1-ylidene)methylideneazanide

Base Information

• Chemical Name: Bromozinc(1+);(6-methylidenecyclohexa-2,4-dien-1-ylidene)methylideneazanide
• CAS No.: 199465-66-2
• Molecular Formula: C8H6BrNZn
• Molecular Weight: 261.42400
• DSSTox Substance ID: DTXSID30408055
• Mol file: 199465-66-2.mol

Synonyms:bromozinc(1+);(6-methylidenecyclohexa-2,4-dien-1-ylidene)methylideneazanide;DTXSID30408055;J-012880

Chemical Property of Bromozinc(1+);(6-methylidenecyclohexa-2,4-dien-1-ylidene)methylideneazanide

Chemical Property:

• Vapor Pressure: 0.243mmHg at 25°C
• Boiling Point: 206oC at 760 mmHg
• Flash Point: 1 °F
• PSA: 23.79000
• Density: 0.993 g/mL at 25oC
• LogP: 2.71708
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 258.89750
• Heavy Atom Count: 11
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

2-Cyanobenzylzinc bromide solution 0.5M in THF ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 14-19-22-36/38-40-36/37-11
• Safety Statements: 16-26-33-36-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=C1C=CC=CC1=C=[N-].[Zn+]Br
• Uses: 2-Cyanobenzylzinc bromide can be used as a reactant: In the metal-catalyzed Negishi cross-coupling reactions to prepare aryl or heteroaryl derivatives via carbon-carbon bond formation. To synthesize 4-(2-Cyanobenzyl)-3′-(trifluoromethyl)biphenyl by reacting with aryl nonaflate in the presence of Pd(dba)2 as a catalyst. To prepare 2-[(2-cyanophenyl)methyl] benzamide by treating with 2-iodobenzamide using a nickel catalyst.

Technology Process of Bromozinc(1+);(6-methylidenecyclohexa-2,4-dien-1-ylidene)methylideneazanide

There total 2 articles about Bromozinc(1+);(6-methylidenecyclohexa-2,4-dien-1-ylidene)methylideneazanide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-(bromomethyl)benzonitrile (22115-41-9) + zinc (7440-66-6) → 2-cyano-benzylzinc bromide (199465-66-2)

Guidance literature:

In tetrahydrofuran; at 40 ℃; Inert atmosphere;

DOI:10.1002/anie.201802656

Reference yield:

→ 2-cyano-benzylzinc bromide (199465-66-2)

Guidance literature:

With chloro-trimethyl-silane; In tetrahydrofuran; ethylene dibromide; at 65 ℃; for 0.5h; Inert atmosphere;

In tetrahydrofuran; ethylene dibromide; at 20 ℃; for 1h; Inert atmosphere;

Reference yield: 90.0%

2-cyano-benzylzinc bromide (199465-66-2) + 3-bromo-5-(trifluoromethyl)pyridine (436799-33-6) → 2-[[5-(trifluoromethyl)-3-pyridyl]methyl]benzonitrile

Guidance literature:

With (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; N,N-dimethyl-formamide; at 60 ℃; for 0.333333h; under 2625.26 - 3000.3 Torr; Irradiation; Flow reactor;

DOI:10.1002/anie.201802656

upstream raw materials:

2-(bromomethyl)benzonitrile

zinc

Downstream raw materials:

{(S)-6-[(R)-4-(2-cyano-benzyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester