Methyl 3-(2-hydroxyphenyl)prop-2-enoate

Base Information

• Chemical Name: Methyl 3-(2-hydroxyphenyl)prop-2-enoate
• CAS No.: 20883-98-1
• Molecular Formula: C10H10 O3
• Molecular Weight: 178.188
• Hs Code.: 2918290000
• DSSTox Substance ID: DTXSID90943139
• Wikidata: Q105350801
• Mol file: 20883-98-1.mol

Synonyms:methyl ortho-hydroxycinnamate;methyl 3-(2-hydroxyphenyl)prop-2-enoate;20883-98-1;methyl 2-hydroxycinnamate;2-Propenoic acid, 3-(2-hydroxyphenyl)-, methyl ester;DTXSID90943139;YMXREWKKROWOSO-UHFFFAOYSA-N;methyl 3-(2-hydroxyphenyl)acrylate;methyl 3-(2'-hydroxyphenyl)-2-propenate;FT-0638059;3-(2-HYDROXY-PHENYL)-ACRYLICACIDMETHYLESTER

Chemical Property of Methyl 3-(2-hydroxyphenyl)prop-2-enoate

Chemical Property:

• Vapor Pressure: 0.000379mmHg at 25°C
• Melting Point: 119-120 °C
• Boiling Point: 308.2°Cat760mmHg
• PKA: 8.56±0.30(Predicted)
• Flash Point: 133.7°C
• PSA: 46.53000
• Density: 1.197g/cm³
• LogP: 1.57840
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 198

Purity/Quality:

98% ^*data from raw suppliers

Methyl2-Hydroxycinnamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CC1=CC=CC=C1O

Technology Process of Methyl 3-(2-hydroxyphenyl)prop-2-enoate

There total 15 articles about Methyl 3-(2-hydroxyphenyl)prop-2-enoate 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: 100.0%

2-Iodophenol (533-58-4) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 2-coumarate (20883-98-1)

Guidance literature:

With palladium diacetate; triethylamine; In acetonitrile; at 70 ℃; for 40h; Inert atmosphere;

DOI:10.1021/jo1010922

Reference yield: 99.5%

methanol (67-56-1) + 2-hydroxycinnamic acid (495-79-4,583-17-5,614-60-8) → methyl 2-coumarate (20883-98-1)

Guidance literature:

With chloro-trimethyl-silane; at 0 - 20 ℃;

DOI:10.1021/jf901176m

Reference yield: 91.0%

salicylaldehyde (90-02-8) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl 2-coumarate (20883-98-1)

Guidance literature:

In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol401240z

upstream raw materials:

(2-hydroxyphenyl)mercury chloride

acrylic acid methyl ester

salicylaldehyde

methyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

coumarin

(E)-3-(2-Oxiranylmethoxy-phenyl)-acrylic acid methyl ester

C₂₈H₃₈N₄O₄

C₂₃H₂₉NO₆

Refernces

• 1、 Pünk?sti, Zoltán,Kele, Péter,Herner, András. "Synthesis of 7-Azido-3-Formylcoumarin – A Key Precursor in Bioorthogonally Applicable Fluorogenic Dye Synthesis". supporting information. p. 1183 - 1188. Retrieved 2018/03/21.
• 2、 Konrádová, Daniela,Kozubíková, Hana,Dole?al, Karel,Pospí?il, Ji?í. "Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol". . p. 5204 - 5213. Retrieved 2017/09/29.