4-Cyanocinnamic acid

Base Information

• Chemical Name: 4-Cyanocinnamic acid
• CAS No.: 16642-94-7
• Molecular Formula: C₁₀H₇NO₂
• Molecular Weight: 173.171
• Hs Code.: 2916399090
• European Community (EC) Number: 242-484-8,812-449-7
• NSC Number: 134574
• DSSTox Substance ID: DTXSID801277921
• Nikkaji Number: J1.595.848K,J222.266C
• Mol file: 16642-94-7.mol

Synonyms:4-Cyanocinnamic acid;18664-39-6;16642-94-7;3-(4-cyanophenyl)acrylic acid;(E)-3-(4-Cyanophenyl)acrylic acid;trans-4-Cyanocinnamic acid;3-(4-cyanophenyl)prop-2-enoic acid;(E)-3-(4-cyanophenyl)prop-2-enoic acid;(2E)-3-(4-cyanophenyl)prop-2-enoic acid;MFCD00016845;EINECS 242-484-8;3-(4-Cyanophenyl)propenoic acid;(E)-3-(4-Cyanophenyl)acrylicacid;(E)-4-cyanocinnamic acid;2-Propenoic acid, 3-(4-cyanophenyl)-, (E)-;MLS001002945;SCHEMBL992032;SCHEMBL992033;JS-186C;DTXSID801277921;HMS1775I18;HMS2765O17;NSC134574;AKOS000263553;AKOS025310784;NSC-134574;(E)-3-(4-cyano-phenyl)-acrylic acid;NCGC00246172-01;SMR000372599;(2e)-3-(4-cyanophenyl)-2-propenoic acid;CS-0100042;EN300-11184;EN300-832893;AG-664/01337012;(E)-3-(4-cyano-phenyl)-acrylic acid, AldrichCPR;J-501915;Z2942851604

Chemical Property of 4-Cyanocinnamic acid

Chemical Property:

• Vapor Pressure: 1.82E-06mmHg at 25°C
• Melting Point: 245-248
• Boiling Point: 380.4°Cat760mmHg
• PKA: 4.13±0.10(Predicted)
• Flash Point: 183.9°C
• Density: 1.26g/cm³
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 173.047678466
• Heavy Atom Count: 13
• Complexity: 253

Purity/Quality:

98% ^*data from raw suppliers

3-(4-Cyanophenyl)acrylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)C#N
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)O)C#N

Technology Process of 4-Cyanocinnamic acid

There total 16 articles about 4-Cyanocinnamic 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: 99.0%

acetic acid (64-19-7,77671-22-8) + 4-cyanobenzaldehyde (105-07-7) → (E)-4-cyanocinnamic acid (16642-94-7,18664-39-6)

Guidance literature:

acetic acid; 4-cyanobenzaldehyde; With titanium tetrachloride; In dichloromethane; at 25 ℃; for 0.333333h; Inert atmosphere;

With triethylamine; In dichloromethane; at 25 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.04.098

Reference yield: 95.0%

malonic acid (141-82-2) + 4-cyanobenzaldehyde (105-07-7) → (E)-4-cyanocinnamic acid (16642-94-7,18664-39-6)

Guidance literature:

With piperidine; pyridine; at 110 ℃; for 2h; Inert atmosphere;

Reference yield: 92.6%

p-nitrobenzyl 4-cyanocinnamate (133430-47-4) → (E)-4-cyanocinnamic acid (16642-94-7,18664-39-6)

Guidance literature:

upstream raw materials:

malonic acid

4-cyanobenzaldehyde

acetic anhydride

(trimethylsilyl)ketene bis(trimethylsilyl) acetal

Downstream raw materials:

(E)-4-cyanocinnamoyl chloride

4'-bromo-2'-methyl-cis-stilbene-carbonitrile-⁽⁴⁾

(1R,2S,3R,4S)-3,4-Bis-(4-cyano-phenyl)-cyclobutane-1,2-dicarboxylic acid

2-methyl-cis-stilbene-dicarbonitrile-(4.4')

Refernces

• 1、 Bezerra Fran?a, Saraliny,Carine Barros de Lima, Luana,Rychard da Silva Cunha, Cristhyan,Santos Anuncia??o, Daniela,Ferreira da Silva-Júnior, Edeildo,Ester de Sá Barreto Barros, Maria,José da Paz Lima, Dimas. "Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae)". . . Retrieved 2021/07/07.
• 2、 Gao, Yang,Zhang, Peng,Cui, Anfeng,Ye, De-Yong,Xiang, Meng,Chu, Yong. "Discovery and anti-inflammatory evaluation of benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of glycogen synthase kinase-3β (GSK-3β)". . p. 5479 - 5493. Retrieved 2018/10/09.