3-Bromocinnamic acid

Base Information

• Chemical Name: 3-Bromocinnamic acid
• CAS No.: 14473-91-7
• Molecular Formula: C9H7BrO2
• Molecular Weight: 227.057
• Hs Code.: 2916399090
• European Community (EC) Number: 251-267-7,678-051-9
• NSC Number: 102779
• DSSTox Substance ID: DTXSID4067729,DTXSID301034663
• Nikkaji Number: J1.276.282H,J55.413H
• Wikidata: Q106902975
• Mol file: 14473-91-7.mol

Synonyms:3-bromocinnamic acid;3-bromocinnamic acid, (E)-isomer;3-bromocinnamic acid, monoacid;3-bromocinnamic acid, silver (+1) salt;meta-bromocinnamic acid

Chemical Property of 3-Bromocinnamic acid

Chemical Property:

• Vapor Pressure: 2.57E-05mmHg at 25°C
• Melting Point: 177-179 °C(lit.)
• Boiling Point: 344.088 °C at 760 mmHg
• Flash Point: 161.899 °C
• PSA: 37.30000
• Density: 1.608 g/cm³
• LogP: 2.54690
• Water Solubility.: Insoluble in water.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 225.96294
• Heavy Atom Count: 12
• Complexity: 189

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-BromocinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)Br)C=CC(=O)O
• Isomeric SMILES: C1=CC(=CC(=C1)Br)/C=C/C(=O)O
• Uses: trans-3-Bromocinnamic acid is used as organic synthesis of raw materials, fine chemicals, pharmaceutical intermediates.

Technology Process of 3-Bromocinnamic acid

There total 15 articles about 3-Bromocinnamic acid 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: 95.0%

m-bromobenzoic aldehyde (3132-99-8) + malonic acid (141-82-2) → 3-bromocinnamic acid (14473-91-7,20595-41-9,32862-97-8)

Guidance literature:

With piperidine; pyridine; at 100 ℃; for 1.5h;

DOI:10.1039/b812001c

Reference yield: 95.0%

m-bromobenzoic aldehyde (3132-99-8) + malonic acid (141-82-2) → 3-Bromocinnamic acid (14473-91-7)

Guidance literature:

With piperidine; pyridine; at 100 ℃; for 1.5h;

DOI:10.1002/chem.200500648

Reference yield: 94.0%

cycl-isopropylidene malonate (2033-24-1) + m-bromobenzoic aldehyde (3132-99-8) → 3-bromocinnamic acid (14473-91-7,20595-41-9,32862-97-8)

Guidance literature:

With hydroxy sulfonylurea; In neat (no solvent); at 110 ℃; for 0.166667h; Reagent/catalyst; Green chemistry;

DOI:10.1039/c5ra14001c

upstream raw materials:

m-aminocinnamic acid

m-bromobenzoic aldehyde

acetic anhydride

3-nitro-benzaldehyde

Downstream raw materials:

methyl 3-(3'-bromophenyl)-acrylate

6-amino-5-(3-bromocinnamoylamino)-3-propargyluracil

3-(3-bromophenyl)propanoic acid

m-bromobenzoic aldehyde

Refernces

• 1、 Liu, Yue,Li, Peng-Xiao,Mu, Wen-Wen,Sun, Ya-Lei,Liu, Ren-Min,Yang, Jie,Liu, Guo-Yun. "Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives". . . Retrieved 2022/01/13.
• 2、 Xu, Hehuan,Liu, Jiayu,Nie, Feiyun,Zhao, Xiaowei,Jiang, Zhiyong. "Metal-Free Hydropyridylation of Thioester-Activated Alkenes via Electroreductive Radical Coupling". . p. 16204 - 16212. Retrieved 2021/10/25.