3-(4-Chlorophenyl)-2-cyanoacrylic acid

Base Information

• Chemical Name: 3-(4-Chlorophenyl)-2-cyanoacrylic acid
• CAS No.: 20374-46-3
• Molecular Formula: C10H5ClNO2-
• Molecular Weight: 207.616
• Hs Code.: 2926909090
• European Community (EC) Number: 830-876-7
• Nikkaji Number: J2.635.271A
• ChEMBL ID: CHEMBL3582403
• Mol file: 20374-46-3.mol

Synonyms:4-chloro-alpha-cyanocinnamic acid;Cl-CCA cpd

Chemical Property of 3-(4-Chlorophenyl)-2-cyanoacrylic acid

Chemical Property:

• Vapor Pressure: 2.36E-06mmHg at 25°C
• Melting Point: 191-193
• Boiling Point: 377 °C at 760 mmHg
• PKA: 0.55±0.10(Predicted)
• Flash Point: 181.8 °C
• PSA: 61.09000
• Density: 1.415±0.06 g/cm3(Predicted)
• LogP: 2.33158
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 207.0087061
• Heavy Atom Count: 14
• Complexity: 295

Purity/Quality:

98%min ^*data from raw suppliers

4-Chloro-α-cyanocinnamic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=C(C#N)C(=O)O)Cl
• Isomeric SMILES: C1=CC(=CC=C1/C=C(\C#N)/C(=O)O)Cl
• Description: 4-chloro-α-cyanocinnamic acid (Cl-CCA) is a phenylpropanoid, related to cinnamic acid, which is synthesized by plants from phenylalanine. Cl-CCA readily co-crystallizes with various biomolecules (e.g., peptides, nucleic acids, etc.).
• Uses: 4-Chloro-α-cyanocinnamic Acid (cas# 20374-46-3) is a compound useful in organic synthesis.

Technology Process of 3-(4-Chlorophenyl)-2-cyanoacrylic acid

There total 10 articles about 3-(4-Chlorophenyl)-2-cyanoacrylic 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: 98.0%

4-chlorobenzaldehyde (104-88-1) + cyanoacetic acid (372-09-8) → 3-(4-chlorophenyl)-2-cyanoacrylic acid (69727-07-7,20374-46-3)

Guidance literature:

hexan-1-amine; In benzene; for 30h; Heating; azeotropic water removal;

DOI:10.1016/S0040-4020(01)91880-0

Reference yield: 56.0%

trimethylsilyl cyanide (7677-24-9) + (4-chlorophenyl)propiolic acid (3240-10-6) → 2-cyano-3-(p-chlorophenyl)propenoic acid (20374-46-3)

Guidance literature:

With diphenyl(methyl)phosphine; In toluene; at 20 ℃; for 16h; stereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.tet.2021.132457

Reference yield: 23.0%

4-chlorobenzaldehyde (104-88-1) + cyanoacetic acid (372-09-8) → 2-cyano-3-(p-chlorophenyl)propenoic acid (20374-46-3)

Guidance literature:

With Tonsil Actisil FF; at 80 ℃; for 0.75h; Irradiation;

DOI:10.1080/00397919808004530

upstream raw materials:

4-chlorobenzaldehyde

cyanoacetic acid

trimethylsilyl cyanide

(4-chlorophenyl)propiolic acid

Downstream raw materials:

4-chlorocinnamonitrile

carbon dioxide

[(E)-3-(4-Chloro-phenyl)-2-cyano-acryloyl]-urea

cyanoacetate

Refernces

• 1、 Meyer, Maximilian,Peri?, Milica,Sch?mberg, Fritz,Vilotijevi?, Ivan. "trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines". supporting information. . Retrieved 2021/10/04.
• 2、 Gurrapu, Shirisha,Jonnalagadda, Sravan K.,Alam, Mohammad A.,Nelson, Grady L.,Sneve, Mary G.,Drewes, Lester R.,Mereddy, Venkatram R.. "Monocarboxylate transporter 1 inhibitors as potential anticancer agents". . p. 558 - 561. Retrieved 2015/05/27.