3-Cyanocinnamic acid

Base Information

• Chemical Name: 3-Cyanocinnamic acid
• CAS No.: 16642-93-6
• Molecular Formula: C10H7NO2
• Molecular Weight: 173.171
• Hs Code.: 2926909090
• Mol file: 16642-93-6.mol

Synonyms:2-Propenoicacid, 3-(3-cyanophenyl)-, (E)-;Cinnamic acid, m-cyano-, (E)- (8CI);(2E)-3-(3-Cyanophenyl)-2-propenoic acid;trans-3-(3-Cyanophenyl)-2-propenoicacid;trans-3-(3-Cyanophenyl)acrylic acid;3-Cyanocinnamic acid;

Chemical Property of 3-Cyanocinnamic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.597
• Boiling Point: 357.908 °C at 760 mmHg
• PKA: 4.20±0.10(Predicted)
• Flash Point: 170.257 °C
• PSA: 61.09000
• Density: 1.262 g/cm³
• LogP: 1.65608
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

3-CyanocinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3-Cyanocinnamic Acid was used to synthesize triazoles with antifungal activities. It was also used to prepare aminocyclohexylethyl-substituted methylsulfonyloxy and methylsulfonyl tetrahydrobenzazepines as dopamine receptor antagonists and antipsychotics.

Technology Process of 3-Cyanocinnamic acid

There total 9 articles about 3-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: 82.0%

3-cyanobromobenzene (6952-59-6) + acrylic acid (79-10-7) → (3E)-3-(3-cyanophenyl)acrylic acid (16642-93-6)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In acetonitrile; at 180 ℃; for 0.25h; Microwave irradiation; Sealed tube;

DOI:10.1021/op034075+

Reference yield: 81.0%

malonic acid (141-82-2) + 3-Cyanobenzaldehyde (24964-64-5) → (3E)-3-(3-cyanophenyl)acrylic acid (16642-93-6)

Guidance literature:

malonic acid; 3-Cyanobenzaldehyde; With piperidine; pyridine; at 100 ℃; for 4h;

With hydrogenchloride; In water; at 20 ℃;

DOI:10.1016/j.ejmech.2011.08.036

Reference yield:

3-(3-cyano-phenyl)-acrylic acid methyl ester (193151-10-9) → (3E)-3-(3-cyanophenyl)acrylic acid (16642-93-6)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water;

upstream raw materials:

malonic acid

3-Cyanobenzaldehyde

3-Methylbenzonitrile

water

Downstream raw materials:

3-(3-cyano-phenyl)-acrylic acid methyl ester

3-(3-cyanophenyl)-2-(E)-propen-1-ol

(E)-N-(4-{4-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]piperazin-1-yl}phenyl)-3-(3-cyanophenyl)acrylamide

(2E)-N-(3-bromophenyl)-3-(3-cyanophenyl)prop-2-enamide

Refernces

• 1、 Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.. "Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes". supporting information. p. 9413 - 9418. Retrieved 2021/12/09.
• 2、 Legoabe, Lesetja,Kruger, Johann,Petzer, Anél,Bergh, Jacobus J.,Petzer, Jacobus P.. "Monoamine oxidase inhibition by selected anilide derivatives". experimental part. p. 5162 - 5174. Retrieved 2011/11/29.