Benzoylformic acid

Base Information

• Chemical Name: Benzoylformic acid
• CAS No.: 611-73-4
• Molecular Formula: C8H6O3
• Molecular Weight: 150.134
• Hs Code.: 29183000
• European Community (EC) Number: 210-278-7
• NSC Number: 28293
• UNII: 2PZL5A0W0M
• DSSTox Substance ID: DTXSID80209993
• Nikkaji Number: J2.992K
• Wikipedia: Phenylglyoxylic_acid
• Wikidata: Q663909
• NCI Thesaurus Code: C173424
• Metabolomics Workbench ID: 37877
• ChEMBL ID: CHEMBL950
• Mol file: 611-73-4.mol

Synonyms:benzoylformate;benzoylformic acid;phenylglyoxilic acid;phenylglyoxylic acid;phenylglyoxylic acid, calcium salt;phenylglyoxylic acid, potassium salt;phenylglyoxylic acid, sodium salt;phenylglyoxylic hydrochloride

Chemical Property of Benzoylformic acid

Chemical Property:

• Appearance/Colour: white to light yellow adhering crystals
• Vapor Pressure: 0.00697mmHg at 25°C
• Melting Point: 60-69 °C
• Refractive Index: 1.568
• Boiling Point: 258.6 °C at 760 mmHg
• PKA: 2.15±0.54(Predicted)
• Flash Point: 124.4 °C
• PSA: 54.37000
• Density: 1.298 g/cm³
• LogP: 0.95390
• Storage Temp.: Refrigerator
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: very faint turbidity
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 150.031694049
• Heavy Atom Count: 11
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

Phenylglyoxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-28-36-28A-24-22-37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C=C1)C(=O)C(=O)O
• Uses: Phenylglyoxylic Acid (cas# 611-73-4) is a compound useful in organic synthesis. Phenylglyoxylic acid can be used as a precursor in the synthesis of: O-acyl acetanilides by decarboxylative o-acylation of acetanilides using Pd catalyst.Phenylhydroxycarbene by high-vacuum flash pyrolysis.2-arylbenzothiazoles by reacting with o-aminothiophenol using ammonium niobium oxalate (ANO) as a catalyst.3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones by treating with o-aminophenol in the presence of ammonium niobium oxalate catalyst.2-aryl benzothiazoles through potassium persulfate (K2S2O8)-mediated oxidative condensation of benzothiazoles.

Technology Process of Benzoylformic acid

There total 290 articles about Benzoylformic 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: 94.0%

2-hydroxy-4-methyl-2-phenylmorpholin-3-one → Benzoylformic acid (611-73-4)

Guidance literature:

With hydrogenchloride; for 2h; Heating;

DOI:10.1246/bcsj.69.2079

Reference yield: 82.0%

phenylglycin (2835-06-5) → Benzoylformic acid (611-73-4)

Guidance literature:

With potassiuim nitrosodisulfonate; In water; for 60h; pH 10.0;

DOI:10.1021/jo00372a033

Reference yield: 75.4%

3,5-diphenyl-4,4-dichloro-5-hydroxy-Δ2-isoxazoline (79344-05-1) → benzonitrile (100-47-0) + Benzoylformic acid (611-73-4)

Guidance literature:

With potassium hydroxide; In water; for 2.5h; Heating;

upstream raw materials:

styrene

benzoyl cyanide

phenylglyoxylic acid ethyl ester

methanol

Downstream raw materials:

Phenyl-[(Z)-[1,2,4]triazol-4-ylimino]-acetic acid

5-benzoylpyrazinecarboxamide

(3,4-dihydroisoquinoline-2(1H)-yl)(phenyl)methanethione

phenyl(pyrazin-2-yl)methanone

Refernces

Dichloromethane as a methylene synthon for regioselective linkage of diverse carboxylic acids: Direct access to methylene diesters under metal-free conditions

10.1016/j.cclet.2019.04.053

This study presents a metal-free cross-coupling protocol for synthesizing methylene diesters from carboxylic acids using dichloromethane (DCM) as a methylene synthon and potassium carbonate (K2CO3) as the sole additive. The researchers optimized the reaction conditions, finding that using 2 equivalents of K2CO3 at 130 °C for 5 hours under an air atmosphere provided the best results. The method demonstrated good functional group tolerance and was effective for a wide range of carboxylic acids, including alkyl, a,?-unsaturated, heteroaryl, and a-oxobenzeneacetic acids, as well as benzoic acids with various substituents. The study also included a gram-scale synthesis to evaluate the protocol's practicality, which showed promising results for large-scale applications. The proposed mechanism involves the formation of potassium carboxylate salt from the carboxylic acid, followed by a nucleophilic attack on DCM to form the methylene diester.