3-Fluoro-2-oxopropanoic acid

Base Information

• Chemical Name: 3-Fluoro-2-oxopropanoic acid
• CAS No.: 433-48-7
• Molecular Formula: C3H3 F O3
• Molecular Weight: 106.053
• Hs Code.: 2918300090
• NSC Number: 21734
• UNII: 040OM3QF5R
• DSSTox Substance ID: DTXSID30962985
• Nikkaji Number: J49.680D
• Wikidata: Q27124338
• Metabolomics Workbench ID: 58882
• ChEMBL ID: CHEMBL1162543
• Mol file: 433-48-7.mol

Synonyms:3-fluoropyruvate;3-fluoropyruvate, sodium salt

Chemical Property of 3-Fluoro-2-oxopropanoic acid

Chemical Property:

• Vapor Pressure: 0.566mmHg at 25°C
• Boiling Point: 174.9°Cat760mmHg
• Flash Point: 59.6°C
• PSA: 54.37000
• Density: 1.409g/cm³
• LogP: -0.39040
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 106.00662212
• Heavy Atom Count: 7
• Complexity: 98.4

Purity/Quality:

98%min ^*data from raw suppliers

3-FluoropyruvicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(C(=O)C(=O)O)F
• Uses: 3-Fluoropyruvic Acid is a useful building block and has been proposed to have a mechanistic effect on the inactivation of mandelate racemase.

Technology Process of 3-Fluoro-2-oxopropanoic acid

There total 3 articles about 3-Fluoro-2-oxopropanoic 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:

3-fluoroalanine (16652-37-2,43163-93-5) → fluoropyruvic acid (433-48-7) + (R)-3-fluoroalanine (35455-21-1,43163-93-5) + (S)-3-fluoroalanine (35455-20-0,43163-93-5) + (R)-3-fluorolactic acid (3130-92-5)

Guidance literature:

With L-lactate dehydrogenase; Bacillus subtilis L-alanine dehydrogenase; nicotinamide adenine dinucleotide; In aq. phosphate buffer; at 25 ℃; pH=7.9;

DOI:10.1021/op060027o

Reference yield:

3-fluoroalanine (16652-37-2,43163-93-5) → fluoropyruvic acid (433-48-7) + (R)-3-fluoroalanine (35455-21-1,43163-93-5)

Guidance literature:

With recombinant C-terminally hexahistidine-tagged Rhodotorula gracilis D-amino acid oxidase-Vitreoscilla hemoglobin fusion protein; oxygen; flavin adenine dinucleotide; catalase; at 25 ℃; for 15h; pH=8; Reagent/catalyst; Concentration; Time; optical yield given as %ee; enantioselective reaction; Kinetics; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1271/bbb.110122

Reference yield:

Diethyl fluoroxaloacetate (392-58-5) → fluoropyruvic acid (433-48-7) + monofluoro-oxaloacetate (392-47-2)

Guidance literature:

With hydrogenchloride; acetic acid; at 5 ℃; for 600h; Yields of byproduct given;

upstream raw materials:

Diethyl fluoroxaloacetate

3-fluoroalanine

Downstream raw materials:

fluoro-pyruvic acid methyl ester

(S)-3-fluoroalanine

2-oxo-propionic acid

(R)-3-fluoroalanine

Refernces

• 1、 Goncalves, Luciana P. B.,Antunes,Oestreicher, Enrique G.. "Thermodynamics and kinetic aspects involved in the enzymatic resolution of (R,S)-3-fluoroalanine in a coupled system of redox reactions catalyzed by dehydrogenases". . p. 673 - 677. Retrieved 2012/12/22.