4-[Hydroxy(methyl)phosphoryl]-2-oxobutanoic acid

Base Information

• Chemical Name: 4-[Hydroxy(methyl)phosphoryl]-2-oxobutanoic acid
• CAS No.: 79778-02-2
• Molecular Formula: C5H9O5P
• Molecular Weight: 180.097
• Nikkaji Number: J153.968J
• Wikidata: Q27124343
• Metabolomics Workbench ID: 58886
• Mol file: 79778-02-2.mol

Synonyms:4-[hydroxy(methyl)phosphoryl]-2-oxobutanoic acid;4-(hydroxymethylphosphinyl)-2-oxobutyric acid;4-(hydroxymethylphosphinyl)-2-oxobutanoic acid;Butanoic acid, 4-(hydroxymethylphosphinyl)-2-oxo-;SCHEMBL2399493;CHEBI:55526;AKOS006276885;4-(Methylhydroxyphosphinyl)-2-oxobutyric acid;4-(methylhydroxyphosphinyl)-2-ketobutyric acid;F84270;Q27124343

Chemical Property of 4-[Hydroxy(methyl)phosphoryl]-2-oxobutanoic acid

Chemical Property:

• Melting Point: 101 °C(Solv: ethyl ether (60-29-7); acetone (67-64-1))
• Boiling Point: 481.8±28.0 °C(Predicted)
• PKA: 2.45±0.54(Predicted)
• PSA: 125.81000
• Density: 1.446±0.06 g/cm3(Predicted)
• LogP: -0.19260
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 180.01876038
• Heavy Atom Count: 11
• Complexity: 221

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CP(=O)(CCC(=O)C(=O)O)O

Technology Process of 4-[Hydroxy(methyl)phosphoryl]-2-oxobutanoic acid

There total 26 articles about 4-[Hydroxy(methyl)phosphoryl]-2-oxobutanoic 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: 98.0%

C5H7O4P → 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid (79778-02-2)

Guidance literature:

In tetrahydrofuran; at 10 - 55 ℃; for 2h; Temperature; Solvent;

Reference yield: 97.3%

2-4-((ethoxy)(methyl)phosphoryl)butanone (73870-64-1) → 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid (79778-02-2)

Guidance literature:

With potassium permanganate; potassium hydroxide; In water; at 0 - 50 ℃; for 3.5h; Reagent/catalyst; Temperature;

Reference yield: 94.6%

methyldichlorophosphane (676-83-5) + ethyl 2-oxobut-3-enoate (134745-23-6) → 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid (79778-02-2)

Guidance literature:

methyldichlorophosphane; ethyl 2-oxobut-3-enoate; With triethylamine; In ethanol; at 10 ℃; for 1h;

With sodium hydroxide; In ethanol; water; for 5h; Temperature; Solvent; Reflux;

upstream raw materials:

ethyl 3-(ethoxymethylphosphinyl)propionate

oxalic acid diethyl ester

methyl(2-oxamoylethyl)phosphinic acid

trimethylsilyl methyl(3-trimethylsiloxy-3-cyano-2-propenyl)phosphinate

Downstream raw materials:

ammonium glufosinate

4-[hydroxy(methyl)phosphonyl]-DL-homoalanine

L-phosphinothricin

α-ketoglutaric acid

Refernces

• 1、 -. "METHODS FOR IMPROVING YIELDS OF L-GLUFOSINATE". Page/Page column 3; 33. . Retrieved 2020/03/29.
• 2、 -. "Efficient purification process of 4-(methylhydroxyphosphoryl)-2-carbonylbutyric acid". Paragraph 0035; 0037; 0038; 0040; 0041; 0043; 0044; 0046. . Retrieved 2019/03/06.