Ethyl 3-[2-(bromomethyl)phenyl]prop-2-enoate

Base Information

• Chemical Name: Ethyl 3-[2-(bromomethyl)phenyl]prop-2-enoate
• CAS No.: 60633-90-1
• Molecular Formula: C12H13BrO2
• Molecular Weight: 269.138
• DSSTox Substance ID: DTXSID40709904
• Mol file: 60633-90-1.mol

Synonyms:Ethyl 3-[2-(bromomethyl)phenyl]prop-2-enoate;ethyl o-bromomethylcinnamate;ethyl o-(bromomethyl)cinnamate;DTXSID40709904;QHLPDXFUAWWTON-UHFFFAOYSA-N

Chemical Property of Ethyl 3-[2-(bromomethyl)phenyl]prop-2-enoate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 268.00989
• Heavy Atom Count: 15
• Complexity: 226

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC=CC=C1CBr

Technology Process of Ethyl 3-[2-(bromomethyl)phenyl]prop-2-enoate

There total 6 articles about Ethyl 3-[2-(bromomethyl)phenyl]prop-2-enoate 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: 70.0%

ethyl trans-2-methylcinnamate (24393-48-4) → ethyl (E)-3-[2-(bromomethyl)phenyl]-2-propenoate (60633-90-1)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In chloroform; for 18h; Reflux;

DOI:10.1055/s-0039-1690006

Reference yield:

ethyl cinnamate (4192-77-2) → ethyl (E)-3-[2-(bromomethyl)phenyl]-2-propenoate (60633-90-1)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; hexane; ethyl acetate;

Reference yield:

(E)-3-(2-methylphenyl)acrylic acid (939-57-1,2373-76-4,41397-71-1) → ethyl (E)-3-[2-(bromomethyl)phenyl]-2-propenoate (60633-90-1)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂ / CH₂Cl₂ / 2 h / Heating

2: Et₃N / 20 °C

3: NBS; AIBN / CCl₄ / 2 h / Heating

With N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); triethylamine; In tetrachloromethane; dichloromethane;

DOI:10.1016/j.tetlet.2004.07.061

upstream raw materials:

ethyl trans-2-methylcinnamate

(E)-3-(2-methylphenyl)acrylic acid

(E)‐3‐(o‐tolyl)acryloyl chloride

2-methylphenyl aldehyde

Downstream raw materials:

(E)-3-(2-Imidazol-1-ylmethyl-phenyl)-acrylic acid ethyl ester

3-[2-(4-methylsufanylbenzyl)phenyl]acrylic acid ethyl ether

5-<2-(ethoxycarbonylvinyl)benzyl>amino-1,2,3,4-thiatriazole

C₁₃H₁₇N₃O₂S