o-Methylcinnamic acid

Base Information

• Chemical Name: o-Methylcinnamic acid
• CAS No.: 2373-76-4
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID101314786
• Mol file: 2373-76-4.mol

Synonyms:2-Propenoic acid, 3-(2-methylphenyl)-;3-(2-methylphenyl)prop-2-enoic acid;Cinnamic acid, o-methyl-, (E)-;ss-Toluylacrylsaure;2-methyl cinnamic acid;2-Propenoic acid, 3-(2-methylphenyl)-, (E)-;DTXSID101314786;AKOS025116637;SY015112;FT-0613032

Chemical Property of o-Methylcinnamic acid

Chemical Property:

• Appearance/Colour: white flakes or crystal
• Vapor Pressure: 0.000782mmHg at 25°C
• Melting Point: 174-175 °C
• Refractive Index: 1.602
• Boiling Point: 293.5oC at 760 mmHg
• PKA: 4.5(at 25℃)
• Flash Point: 199.3oC
• PSA: 37.30000
• Density: 1.147 g/cm3
• LogP: 2.09280
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: almost transparency in Methanol
• XLogP3: 2.3
• 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:

99% Haccp,,Halal,SC US FDA GMP ISO14001 ^*data from raw suppliers

2-Methylcinnamic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C=CC(=O)O
• Uses: 2-Methylcinnamic acid may be used as starting reagent for the total synthesis of the cytotoxic alkaloid, 22-hydroxyacuminatine and for the preparation of (E)-2-methylcinnamic acid i-butylammonium salt.

Technology Process of o-Methylcinnamic acid

There total 48 articles about o-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: 99.0%

ortho-methylphenyl iodide (615-37-2) + acrylic acid (79-10-7) → (E)-3-(2-methylphenyl)acrylic acid (939-57-1,2373-76-4,41397-71-1)

Guidance literature:

With potassium hydroxide; PS-PEG-NH-C(O)C6H4PPh2-PdCl(η³-C3H5); at 50 ℃;

DOI:10.1055/s-2002-35605

Reference yield: 91.0%

carbon monoxide (201230-82-2) + trans-1-(2-bromovinyl)-2-methylbenzene (889869-30-1) → (E)-3-(2-methylphenyl)acrylic acid (939-57-1,2373-76-4,41397-71-1)

Guidance literature:

With [bmim]PF₆; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In water; at 100 ℃; for 20h; under 15001.2 Torr;

DOI:10.1021/jo052651p

Reference yield: 90.0%

formic acid (64-18-6) + C9H9I → (E)-3-(2-methylphenyl)acrylic acid (939-57-1,2373-76-4,41397-71-1)

Guidance literature:

With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 100 ℃; for 20h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.7b01808

upstream raw materials:

malonic acid

2-methylphenyl aldehyde

methyl (E)-3-(2-methylphenyl)-2-propenoate

7a-Methyl-2-phenylselanyl-2,3,5,7a-tetrahydro-inden-1-one

Downstream raw materials:

3-(2-methylphenyl)propanoic acid

(2RS,3SR)-2,3-dibromo-3-o-tolyl-propionic acid

5,6-dimethoxy-3-(o-tolyl)indan-1-one

2,3-dibromo-3-(o-methylphenyl)propanoic 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、 -. "Method for preparing alpha, beta-unsaturated carboxylic acid compound". Paragraph 0103-0104; 0431-0438. . Retrieved 2021/05/05.