3-Methylcinnamic acid

Base Information

• Chemical Name: 3-Methylcinnamic acid
• CAS No.: 3029-79-6
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Hs Code.: 29163990
• European Community (EC) Number: 221-199-2,621-966-5
• UNII: 377B8288XF
• DSSTox Substance ID: DTXSID001044346
• Nikkaji Number: J135.444B,J205.336E
• Wikidata: Q27130825
• Metabolomics Workbench ID: 61471
• ChEMBL ID: CHEMBL458113
• Mol file: 3029-79-6.mol

Synonyms:3-Methylcinnamic acid;3029-79-6;14473-89-3;(E)-3-(m-Tolyl)acrylic acid;m-Methylcinnamic acid;3-m-Tolylacrylic acid;3-(m-Tolyl)acrylic acid;2-Propenoic acid, 3-(3-methylphenyl)-;(2E)-3-(3-methylphenyl)acrylic acid;(2E)-3-(3-methylphenyl)prop-2-enoic acid;3-Methyl-trans-cinnamic acid;2-Propenoic acid, 3-(3-methylphenyl)-, (2E)-;(E)-3-(3-methylphenyl)prop-2-enoic acid;(2E)-3-(3-Methylphenyl)-2-propenoic acid;trans-m-Methylcinnamic acid;Cinnamic acid, m-methyl-;CHEBI:61118;EINECS 221-199-2;3-(3-methylphenyl)prop-2-enoic acid;3-(3-Methylphenyl)-2-propenoic acid;377B8288XF;MFCD00016844;3-(3-methylphenyl)acrylic acid;3-MethylcinnamicAcid;CinnaMic acid,M-Methyl-;(e)-3-methylcinnamic acid;(E)-3-m-tolylacrylic acid;SCHEMBL79073;(E)-3-m-tolyl-acrylic acid;(E)-3-(m-Tolyl)acrylicacid;CHEMBL458113;UNII-377B8288XF;3-(3-Methylphenyl)propenoic acid;DTXSID001044346;CS-M2096;AC7519;BBL021048;STK893754;AKOS000263597;NCGC00336869-01;AS-38467;AS-63141;M1298;EN300-11154;(2E)-3-(3-Methylphenyl)-2-propenoic acid #;EN300-364980;AB01329805-02;A820304;AE-641/00365055;Q27130825;Z2942851787

Chemical Property of 3-Methylcinnamic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.000572mmHg at 25°C
• Melting Point: 116-119 °C
• Refractive Index: 1.5766 (estimate)
• Boiling Point: 298.3ºC at 760mmHg
• PKA: 4.44(at 25℃)
• Flash Point: 203.9ºC
• PSA: 37.30000
• Density: 1.0281 (rough estimate)
• LogP: 2.09280
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 184

Purity/Quality:

98% ^*data from raw suppliers

3-Methylcinnamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36-24/25-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)C=CC(=O)O
• Isomeric SMILES: CC1=CC(=CC=C1)/C=C/C(=O)O

Technology Process of 3-Methylcinnamic acid

There total 30 articles about 3-Methylcinnamic 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%

3-Iodotoluene (625-95-6) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (E)-3-methylcinnamic acid (3029-79-6,14473-89-3,16642-82-3)

Guidance literature:

With triethylamine; di-(3-methylphenyl)phosphinopolystyrene palladium catalyst; In acetonitrile; at 80 ℃; for 20h;

DOI:10.1002/adsc.200600503

Reference yield: 96.0%

malonic acid (141-82-2) + m-tolyl aldehyde (620-23-5) → (E)-3-methylcinnamic acid (3029-79-6,14473-89-3,16642-82-3)

Guidance literature:

With piperidine; pyridine; for 12h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201403148

Reference yield: 93.0%

meta-bromotoluene (591-17-3) + acrylic acid (79-10-7) → (E)-3-methylcinnamic acid (3029-79-6,14473-89-3,16642-82-3)

Guidance literature:

With tetrabutylammomium bromide; In water; for 12h; Reagent/catalyst; Time; Inert atmosphere; Reflux;

DOI:10.1039/c4nj01581a

upstream raw materials:

acetic anhydride

m-tolyl aldehyde

2-Iodo-3-m-tolyl-propionic acid methyl ester

malonic acid

Downstream raw materials:

(E)-methyl 3-methylcinnamate

Glyoxilic acid

m-tolyl aldehyde

(R,S)-3-amino-3-(3-methylphenyl)propionic acid

Refernces

• 1、 Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei. "Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation". supporting information. p. 5905 - 5908. Retrieved 2021/06/18.
• 2、 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.