2-Chlorocinnamic acid

Base Information

• Chemical Name: 2-Chlorocinnamic acid
• CAS No.: 939-58-2
• Molecular Formula: C₉H₇ClO₂
• Molecular Weight: 182.606
• European Community (EC) Number: 213-363-7,223-154-2
• NSC Number: 98548,98547,52173,4792
• UNII: LT5X82W7YR
• DSSTox Substance ID: DTXSID301035497
• Nikkaji Number: J135.661E,J75.237A
• Mol file: 939-58-2.mol

Synonyms:2-chlorocinnamic acid;trans-2-chlorocinnamic acid

Chemical Property of 2-Chlorocinnamic acid

Chemical Property:

• Melting Point: 212°C
• Refractive Index: 1.5426 (estimate)
• Boiling Point: 321.6°Cat760mmHg
• PKA: 4.29±0.10(Predicted)
• Flash Point: 148.3°C
• PSA: 37.30000
• Density: 1.332g/cm³
• 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:

(E)-3-(2-Chlorophenyl)acrylicacid ^*data from reagent 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-Chlorocinnamic acid

There total 55 articles about 2-Chlorocinnamic 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%

cycl-isopropylidene malonate (2033-24-1) + 2-chloro-benzaldehyde (89-98-5) → o-chlorocinnamic acid (3752-25-8,939-58-2)

Guidance literature:

With 2-carbamoylhydrazine-1-sulfonic acid; In neat (no solvent); at 110 ℃; for 0.333333h; Reagent/catalyst; Green chemistry;

DOI:10.1039/c5ra14001c

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: 93.0%

malonic acid (141-82-2) + 2-chloro-benzaldehyde (89-98-5) → o-chlorocinnamic acid (3752-25-8,939-58-2)

Guidance literature:

With piperidine; pyridine; for 2h; Reflux;

DOI:10.1021/acs.jmedchem.0c02254

upstream raw materials:

2-(2-chlorobenzylidene)malonic acid

2-amino-cinnamic acid

(2RS,3SR)-2,3-dibromo-3-(2-chlorophenyl)propanoic acid

water

Downstream raw materials:

3-(2-chlorophenyl)propanoic acid

(E)-ethyl 2-chlorocinnamate

C₂₃H₂₆ClNO₄

2-chlorocinnamaldehyde