2,3-Dichlorocinnamic acid

Base Information

• Chemical Name: 2,3-Dichlorocinnamic acid
• CAS No.: 20595-44-2
• Molecular Formula: C9H5Cl2O2-
• Molecular Weight: 217.051
• Hs Code.: 2916399090
• European Community (EC) Number: 813-511-6
• Wikidata: Q76145329
• Mol file: 20595-44-2.mol

Synonyms:2,3-Dichlorocinnamic acid;20595-44-2;3-(2,3-Dichlorophenyl)acrylic acid;34164-42-6;(2E)-3-(2,3-dichlorophenyl)prop-2-enoic acid;(E)-3-(2,3-dichlorophenyl)prop-2-enoic acid;trans-2,3-Dichlorocinnamic acid;2-Propenoic acid, 3-(2,3-dichlorophenyl)-, (2E)-;3-(2,3-dichlorophenyl)prop-2-enoic Acid;(2E)-3-(2,3-dichlorophenyl)acrylic acid;(E)-3-(2,3-dichloro-phenyl)-acrylic acid;SCHEMBL1124437;RCEWIEGWGDHVNK-SNAWJCMRSA-N;3-(2,3-Dichlorophenyl)acrylicacid;STR07856;(e)-3-(2,3-dichlorophenyl)acrylic;MFCD01076352;STL554065;AKOS000201775;NCGC00342959-01;(E)-3-(2,3-Dichlorophenyl)acrylic acid;CS-0268617;EN300-07610;C78035;EN300-306592;AB01334886-02;Z56955953

Chemical Property of 2,3-Dichlorocinnamic acid

Chemical Property:

• Vapor Pressure: 6.61E-06mmHg at 25°C
• Melting Point: 229-234oC
• Boiling Point: 363oC at 760 mmHg
• PKA: 4.12±0.10(Predicted)
• Flash Point: 173.3oC
• PSA: 37.30000
• Density: 1.457g/cm3
• LogP: 3.09120
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 215.9744848
• Heavy Atom Count: 13
• Complexity: 216

Purity/Quality:

98.5% ^*data from raw suppliers

2,3-DichlorocinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)Cl)C=CC(=O)O
• Isomeric SMILES: C1=CC(=C(C(=C1)Cl)Cl)/C=C/C(=O)O

Technology Process of 2,3-Dichlorocinnamic acid

There total 5 articles about 2,3-Dichlorocinnamic 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: 94.0%

methyl (E)-3-(2,3-dichlorophenyl)acrylate (175168-68-0) → 3-(2,3-dichlorophenyl)acrylic acid (20595-44-2)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.9b01835

Reference yield: 78.0%

malonic acid (141-82-2) + 2,3-dichlorobenzylaldehyde (6334-18-5) → 3-(2,3-dichlorophenyl)acrylic acid (20595-44-2)

Guidance literature:

With piperidine; pyridine; at 110 ℃;

DOI:10.1016/j.bioorg.2019.01.054

Reference yield:

2,3-dichlorobenzylaldehyde (6334-18-5) → 3-(2,3-dichlorophenyl)acrylic acid (20595-44-2)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 20 °C

2: lithium hydroxide monohydrate / tetrahydrofuran; water / 2 h / 20 °C

With lithium hydroxide monohydrate; In tetrahydrofuran; dichloromethane; water; 1: |Wittig Olefination;

DOI:10.1021/acs.jmedchem.9b01835

upstream raw materials:

acetic anhydride

2,3-dichlorobenzylaldehyde

malonic acid

methyl (E)-3-(2,3-dichlorophenyl)acrylate

Refernces

• 1、 Tan, Liang,Zhou, Qingtong,Yan, Wenzhong,Sun, Jian,Kozikowski, Alan P.,Zhao, Suwen,Huang, Xi-Ping,Cheng, Jianjun. "Design and synthesis of bitopic 2-phenylcyclopropylmethylamine (pcpma) derivatives as selective dopamine d3 receptor ligands". . p. 4579 - 4602. Retrieved 2020/06/08.
• 2、 Chen, Gaozhi,Zhang, Yali,Liu, Xing,Fang, Qilu,Wang, Zhe,Fu, Lili,Liu, Zhiguo,Wang, Yi,Zhao, Yunjie,Li, Xiaokun,Liang, Guang. "Discovery of a New Inhibitor of Myeloid Differentiation 2 from Cinnamamide Derivatives with Anti-Inflammatory Activity in Sepsis and Acute Lung Injury". . p. 2436 - 2451. Retrieved 2016/04/10.