Pyruvic acid, phenyl ester

Base Information

• Chemical Name: Pyruvic acid, phenyl ester
• CAS No.: 2149-49-7
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• DSSTox Substance ID: DTXSID30175790
• Nikkaji Number: J437.580G
• Wikidata: Q83046104
• Mol file: 2149-49-7.mol

Synonyms:Pyruvic acid, phenyl ester;Phenyl pyruvate;2149-49-7;Phenylpyruvate (PPy);SCHEMBL43236;2-Oxopropanoic acid phenyl ester;DTXSID30175790;BDBM154572

Chemical Property of Pyruvic acid, phenyl ester

Chemical Property:

• Vapor Pressure: 0.0326mmHg at 25°C
• Boiling Point: 243.1°Cat760mmHg
• Flash Point: 103.9°C
• Density: 1.166g/cm³
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(=O)OC1=CC=CC=C1

Technology Process of Pyruvic acid, phenyl ester

There total 4 articles about Pyruvic acid, phenyl ester 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%

2-oxo-propionic acid (127-17-3) + phenol (108-95-2,27073-41-2) → methyl phenyl glyoxylate (2149-49-7)

Guidance literature:

With pyridine; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃;

DOI:10.1021/jo00356a026

Reference yield:

Benzoyl bromide (618-32-6) + carbon dioxide (124-38-9,18923-20-1) + methyl iodide (74-88-4) → methyl phenyl glyoxylate (2149-49-7)

Guidance literature:

Benzoyl bromide; carbon dioxide; With 1-butyl-3-methylimidazolium Tetrafluoroborate; Electrochemical reaction;

methyl iodide; at 55 ℃; for 12h;

DOI:10.14233/ajchem.2014.15993

Reference yield:

Sodium; 2-((1R,6R)-6-hydroxy-cyclohexa-2,4-dienyloxy)-acrylate → methyl phenyl glyoxylate (2149-49-7)

Guidance literature:

With benzenesulfonamide; ethylenediaminetetraacetic acid; 2-amino-2-hydroxymethyl-1,3-propanediol; 2-hydroxyethanethiol; In water; at 37 ℃; half-life of rearrangement;

DOI:10.1016/S0960-894X(97)10100-7

upstream raw materials:

2-oxo-propionic acid

phenol

Benzoyl bromide

carbon dioxide

Downstream raw materials:

phenylacetaldehyde

N-α-phenylethylacetamide

(S)-phenyl 2-hydroxy-2-methyl-4-oxopentanoate

Refernces

• 1、 Feng, Qiuju,Tan, Guishan,Li, Yuanjian,Zeng, Wenbin,Yan, Wenbin. "Electrocatalytic carboxylation of benzoyl bromide with CO2 in ionic liquid 1-butyl-3-methyllimidazoliumtetrafluoborate to methyl phenyl glyoxylate". . p. 3241 - 3242. Retrieved 2014.
• 2、 Zhang, Yan-Shun,Gui, Hou-Ze,Wei, Yin,Shi, Min. "Synthesis of Dihydro-2-oxopyrrole (DPO) Building Blocks Catalyzed by Potassium Carbonate". supporting information. p. 7179 - 7185. Retrieved 2019/11/16.