Cinnamic acid, alpha-bromo-, methyl ester

Base Information

• Chemical Name: Cinnamic acid, alpha-bromo-, methyl ester
• CAS No.: 21788-36-3
• Molecular Formula: C10H9BrO2
• Molecular Weight: 241.084
• DSSTox Substance ID: DTXSID501030805
• Nikkaji Number: J193.231D,J2.196.334H
• Mol file: 21788-36-3.mol

Synonyms:21788-36-3;2-bromo-3-phenyl-prop-2-enoic acid methyl ester;methyl (Z)-2-bromo-3-phenylprop-2-enoate;Cinnamic acid, .alpha.-bromo-, methyl ester;UDGLSFZOLJZPTH-CLFYSBASSA-N;DTXSID501030805;24127-62-6;alpha-Bromocinnamic acid methyl ester;AKOS027473686;Methyl (2Z)-2-bromo-3-phenylacrylate;2-Bromo-3-phenylacrylic acid methyl ester;Methyl (2Z)-2-bromo-3-phenyl-2-propenoate;EN300-749094;Methyl (2Z)-2-bromo-3-phenyl-2-propenoate #;EN300-7465606;METHYL (2Z)-2-BROMO-3-PHENYLPROP-2-ENOATE

Chemical Property of Cinnamic acid, alpha-bromo-, methyl ester

Chemical Property:

• Vapor Pressure: 0.00157mmHg at 25°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 239.97859
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C(=CC1=CC=CC=C1)Br
• Isomeric SMILES: COC(=O)/C(=C/C1=CC=CC=C1)/Br

Technology Process of Cinnamic acid, alpha-bromo-, methyl ester

There total 65 articles about Cinnamic acid, alpha-bromo-, methyl ester 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: 99.0%

methyl tribromoacetate (3222-05-7) + benzaldehyde (100-52-7) → methyl 2-bromo-3-phenylacrylate (24127-62-6,21788-35-2,21788-36-3)

Guidance literature:

With chromium dichloride; In tetrahydrofuran; at 23 ℃;

DOI:10.1021/jo061445u

Reference yield: 94.0%

benzaldehyde (100-52-7) + methyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-2-bromoacetate (287481-44-1) → methyl 2-bromo-3-phenylacrylate (24127-62-6,21788-35-2,21788-36-3)

Guidance literature:

methyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-2-bromoacetate; With 18-crown-6 ether; potassium tert-butylate; In tetrahydrofuran; acetonitrile; at -78 ℃; for 0.5h;

benzaldehyde; In tetrahydrofuran; at -78 ℃; for 0.333333h; Further stages.;

DOI:10.1021/ol006074x

Reference yield: 88.0%

benzaldehyde (100-52-7) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl 2-bromo-3-phenylacrylate (24127-62-6,21788-35-2,21788-36-3)

Guidance literature:

methyl (triphenylphosphoranylidene)acetate; In dichloromethane; at 20 ℃; for 1h;

benzaldehyde; With triethylamine; In dichloromethane; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ol702859y

upstream raw materials:

methanol

(Z)-2-bromo-3-phenylacrylic acid

methyl (E)-2-bromo-3-phenylprop-2-enoate

rac-(R,S)-methyl 2,3-dibromo-3-phenylpropanoate

Downstream raw materials:

3-phenyl-2,3-dipiperidino-propionic acid methyl ester

5-Oxo-3-phenyl-tetrahydro-furan-2,4-dicarboxylic acid dimethyl ester

1-Dimethylcarbamoyl-3-phenyl-cyclopropane-1,2-dicarboxylic acid dimethyl ester

(2R,3S,4R,5R)-2-Methyl-3,5-diphenyl-1-aza-bicyclo[2.1.0]pentane-2,4-dicarboxylic acid dimethyl ester