2-Chloro-cis-cinnamic acid

Base Information

• Chemical Name: 2-Chloro-cis-cinnamic acid
• CAS No.: 704-96-1
• Molecular Formula: C9H7ClO2
• Molecular Weight: 182.606
• UNII: JC4B3W5FTM
• DSSTox Substance ID: DTXSID601036082
• Nikkaji Number: J2.177.438C
• Mol file: 704-96-1.mol

Synonyms:2-Chloro-cis-cinnamic acid;(Z)-3-(2-chlorophenyl)prop-2-enoic acid;704-96-1;2-Propenoic acid, 3-(2-chlorophenyl)-, (2Z)-;3-(2-chlorophenyl)acrylic acid;JC4B3W5FTM;o-Chlorocinnamic acid, (Z)-;2-Chlorocinnamic acid, (Z)-;SCHEMBL12852987;DTXSID601036082;Cinnamic acid, o-chloro-, (Z)-;(2Z)-3-(2-Chlorophenyl)-2-propenoic acid;(2Z)-3-(2-chlorophenyl)prop-2-enoic acid;3-(2-Chlorophenyl)-,(Z)-2-propenoic acid;AE-641/01171033

Chemical Property of 2-Chloro-cis-cinnamic acid

Chemical Property:

• Melting Point: 127 °C(Solv: ethanol (64-17-5))
• Boiling Point: 321.6±17.0 °C(Predicted)
• PKA: 4.11±0.10(Predicted)
• PSA: 37.30000
• Density: 1.332±0.06 g/cm3(Predicted)
• LogP: 2.43780
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 182.0134572
• Heavy Atom Count: 12
• Complexity: 189

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Chloro-cis-cinnamic acid

There total 43 articles about 2-Chloro-cis-cinnamic 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: 96.0%

malonic acid (141-82-2) + 2-chloro-benzaldehyde (89-98-5) → trans-2-chlorocinnamic acid (704-96-1,939-58-2)

Guidance literature:

With aluminum oxide; lithium chloride; for 0.0833333h; microwave irradiation;

DOI:10.1081/SCC-120027254

Reference yield: 90.0%

malonic acid (141-82-2) + sodium (2-chlorophenyl)(hydroxy)methanesulfonate → trans-2-chlorocinnamic acid (704-96-1,939-58-2)

Guidance literature:

With piperazine; In ethylene glycol; for 0.1h; microwave irradiation;

Reference yield: 80.0%

2-chloro-benzaldehyde (89-98-5) + acetic acid (64-19-7,77671-22-8) → trans-2-chlorocinnamic acid (704-96-1,939-58-2)

Guidance literature:

With pyridine; dmap; sodium tetraborate decahydrate; N-benzyl-N,N,N-triethylammonium chloride; In 1-methyl-pyrrolidin-2-one; at 185 - 190 ℃; for 8h;

upstream raw materials:

trans-2-chlorocinnamic acid

acetic acid

3-(2'-chlorophenyl)-(Z)-propenoic acid methyl ester

methyl (2E)-3-(2-chlorophenyl)prop-2-enoate

Downstream raw materials:

trans-2-chlorocinnamic acid

3-(2-chlorophenyl)propanoic acid

2-chlorostyrene

(Z)-3-(2-chlorophenyl)acrylic acid

Refernces

• 1、 Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei. "Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation". supporting information. p. 5905 - 5908. Retrieved 2021/06/18.
• 2、 Ghafary, Shahrzad,Ghobadian, Roshanak,Mahdavi, Mohammad,Nadri, Hamid,Moradi, Alireza,Akbarzadeh, Tahmineh,Najafi, Zahra,Sharifzadeh, Mohammad,Edraki, Najmeh,Moghadam, Farshad Homayouni,Amini, Mohsen. "Design, synthesis, and evaluation of novel cinnamic acid-tryptamine hybrid for inhibition of acetylcholinesterase and butyrylcholinesterase". . p. 463 - 477. Retrieved 2020/05/25.