p-Cyanocinnamic acid

Base Information

• Chemical Name: p-Cyanocinnamic acid
• CAS No.: 18664-39-6
• Molecular Formula: C10H7NO2
• Molecular Weight: 173.171
• Hs Code.: 2942000000
• European Community (EC) Number: 242-484-8
• DSSTox Substance ID: DTXSID101296093
• Mol file: 18664-39-6.mol

Synonyms:p-Cyanocinnamic acid;2-Propenoic acid, 3-(4-cyanophenyl)-;EINECS 242-484-8;4-cyano-cinnamic acid;3-(4-cyano-phenyl)-acrylic acid;DTXSID101296093;3-(4-cyanophenyl)-2-propenoic acid;NSC 134574;FT-0600987

Chemical Property of p-Cyanocinnamic acid

Chemical Property:

• Melting Point: 245-248 °C
• Boiling Point: 380.4 °C at 760 mmHg
• PKA: 4.13±0.10(Predicted)
• Flash Point: 183.9 °C
• PSA: 61.09000
• Density: 1.26 g/cm³
• LogP: 1.65608
• Storage Temp.: Sealed in dry,Room Temperature
• 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

4-CyanocinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of p-Cyanocinnamic acid

There total 25 articles about p-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: 97.0%

4-iodobenzonitrile (3058-39-7) + acrylic acid (79-10-7) → 3-(4-cyanophenyl)acrylic acid (18664-39-6)

Guidance literature:

With sodium hydrogencarbonate; In water; at 130 ℃; for 3h;

DOI:10.1039/c4ra01634c

Reference yield: 94.0%

4-bromobenzenecarbonitrile (623-00-7) + acrylic acid (79-10-7) → 3-(4-cyanophenyl)acrylic acid (18664-39-6)

Guidance literature:

With tributyl-amine; at 140 ℃; for 4.5h;

DOI:10.1016/j.reactfunctpolym.2021.104843

upstream raw materials:

potassium acetate

acetic anhydride

4-cyanobenzaldehyde

malonic acid

Downstream raw materials:

(E)-4-cyanocinnamoyl chloride

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

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

4-[(E)-3-Oxo-3-((S)-2-((piperidin-1-yl)methyl)pyrrolidin-1-yl)propenyl]benzonitrile

Refernces

• 1、 Xiao, Jian,Zhang, Haonan,Ejike, Anyaegbu Chima,Wang, Lu,Tao, Minli,Zhang, Wenqin. "Phenanthroline functionalized polyacrylonitrile fiber with Pd(0) nanoparticles as a highly active catalyst for the Heck reaction". . . Retrieved 2021/03/03.
• 2、 Bassetto, Marcella,Brancale, Andrea,Pasqualetto, Gaia,Pileggi, Elisa,Rozanowska, Malgorzata,Schepelmann, Martin,Varricchio, Carmine. "Ligand-based rational design, synthesis and evaluation of novel potential chemical chaperones for opsin". supporting information. . Retrieved 2021/09/24.