(Z)-2-Methyl-3-phenylpropenoic acid

Base Information

• Chemical Name: (Z)-2-Methyl-3-phenylpropenoic acid
• CAS No.: 15250-29-0
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Mol file: 15250-29-0.mol

Synonyms:2-methyl-3c-phenyl-acrylic acid;2-Methyl-3c-phenyl-acrylsaeure;(Z)-2-methyl-3-phenyl-acrylic acid;α-Methyl-cis-zimtsaeure;(Z)-2-methyl-3-phenylacrylic acid;(Z)-2-methyl-3-phenyl-2-propenoic acid;2-Propenoic acid, 2-methyl-3-phenyl-, (Z)-;

Chemical Property of (Z)-2-Methyl-3-phenylpropenoic acid

Chemical Property:

• Melting Point: 94°C
• Refractive Index: 1.5143 (estimate)
• Boiling Point: 288°C (estimate)
• PKA: 4.82±0.10(Predicted)
• PSA: 37.30000
• Density: 1.0613 (rough estimate)
• LogP: 2.17450

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z)-2-Methyl-3-phenylpropenoic acid

There total 12 articles about (Z)-2-Methyl-3-phenylpropenoic 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: 70.0%

ethyl c-α–methylcinnamate (7042-34-4) → (Z)-2-methyl-3-phenylprop-2-enoic acid (15250-29-0)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 20 ℃; for 12h;

DOI:10.1016/j.phytochem.2012.08.001

Reference yield:

ethyl (E)-3-phenyl-2-(trimethylsilylmethyl)prop-2-enoate (680195-78-2) → 2-Benzyl-2-propenoic acid (5669-19-2) + (Z)-2-methyl-3-phenylprop-2-enoic acid (15250-29-0)

Guidance literature:

With potassium hydroxide; water; In methanol; for 3h; Reflux;

DOI:10.1002/hlca.200890093

Reference yield:

1-Phenylprop-1-yne (673-32-5) + carbon dioxide (124-38-9,18923-20-1) → 2-phenyl-trans-crotonic acid (20432-26-2) + (Z)-2-methyl-3-phenylprop-2-enoic acid (15250-29-0) + 2-methyl-3-phenylacrylic acid (1895-97-2)

Guidance literature:

With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine; cobalt(II) bromide; zinc dibromide; 1,2-bis-(dicyclohexylphosphino)ethane; In acetonitrile; at 20 ℃; for 24h; under 760.051 Torr; Reagent/catalyst; Solvent; Overall yield = 70 %; Overall yield = 22.7 mg; Schlenk technique; Irradiation;

DOI:10.1021/jacs.8b01561

upstream raw materials:

2-methyl-3-phenylacrylic acid

benzene diazonium chloride

1-phenylpropadiene

ethyl (E)-3-phenyl-2-(trimethylsilylmethyl)prop-2-enoate

Downstream raw materials:

(±)-1,1′-binaphthyl-2-2′-diyl (Z)-2-methyl-3-phenyl-2-propenoate

2-methyl-1-phenyl-1-propene, β,β-dimethylstyrene

Refernces

• 1、 Abe, Masato,Nishikawa, Keisuke,Okuda, Katsuhiro,Shindo, Mitsuru,Fukuda, Hiroshi,Nakanishi, Kazunari,Tazawa, Yuta,Taniguchi, Tomoya,Park, So-Young,Hiradate, Syuntaro,Fujii, Yoshiharu. "Key structural features of cis-cinnamic acid as an allelochemical". . p. 56 - 67,12. Retrieved 2012/12/12.
• 2、 Rudler, Henri,Durand-Réville, Thomas. "Tungsten(0) alkylidene complexes stabilized as pyridinium ylides: New aspects of their synthesis and reactivity". . p. 571 - 587. Retrieved 2007/10/03.