(E)-1-(2-Bromovinyl)-2-methylbenzene

Base Information

• Chemical Name: (E)-1-(2-Bromovinyl)-2-methylbenzene
• CAS No.: 394698-73-8
• Molecular Formula: C9H9Br
• Molecular Weight: 197.074
• Mol file: 394698-73-8.mol

Synonyms:1-((E)-2-Bromo-vinyl)-2-methyl-benzene;

Chemical Property of (E)-1-(2-Bromovinyl)-2-methylbenzene

Chemical Property:

• Boiling Point: 236.4 °C at 760 mmHg
• Flash Point: 109 °C
• Density: 1.374 g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-(2-Bromovinyl)-2-methylbenzene

There total 3 articles about (E)-1-(2-Bromovinyl)-2-methylbenzene 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: 58.0%

2-methylcinnamic acid (2373-76-4) → 1-(2-bromovinyl)-2-methylbenzene (394698-73-8)

Guidance literature:

With N,N-dimethyl-formamide; potassium bromide; trichlorophosphate; In acetonitrile; at 20 ℃; Reagent/catalyst; Sonication;

DOI:10.1080/15533174.2014.989573

Reference yield:

1,1-dibromo-2-(2-methylphenyl)ethene (104464-03-1) → 1-(2-bromovinyl)-2-methylbenzene (394698-73-8)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; water; at 75 ℃; for 3h; stereoselective reaction;

DOI:10.1055/s-0035-1561558

Reference yield:

2-methylphenyl aldehyde (529-20-4) → 1-(2-bromovinyl)-2-methylbenzene (394698-73-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine / dichloromethane / 0 °C

2: Dimethyl phosphite; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C

With triethylamine; Dimethyl phosphite; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/acs.joc.9b01644

upstream raw materials:

2-methylcinnamic acid

1,1-dibromo-2-(2-methylphenyl)ethene

2-methylphenyl aldehyde

Downstream raw materials:

1-methylphenanthrene

trans-(2-methyl)-1-phenylthiostyrene

trans-1-(2-bromovinyl)-2-methylbenzene

9-(2-methylbenzylidene)-9H-fluorene

Refernces

• 1、 Larin, Egor M.,Lautens, Mark,Marchese, Austin D.,Mirabi, Bijan. "A Simplified Protocol for the Stereospecific Nickel-Catalyzed C-S Vinylation Using NiX 2 Salts and Alkyl Phosphites". . p. 311 - 319. Retrieved 2019/12/28.
• 2、 Kumar, M. Satish,Rajanna,Venkanna,Venkateswarlu,Sudhakar Chary. "Ultrasonically Assisted Decarboxylative Bromination of α,β-Unsaturated Carboxylic Acids under Vilsmeier-Haack Conditions". . p. 642 - 646. Retrieved 2015/12/26.