35597-44-5

Basic information

• Product Name: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)-
• Synonyms: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)-;(S)-2-Amino-4-(hydroxymethylphosphinyl)butyric acid;(S)-4-[Hydroxy(methyl)phosphinyl]-2-aminobutyric acid;(S)-Phosphinothricin;L-Phosphinothricin;Phosphinothricine
• CAS NO: 35597-44-5
• Molecular Formula: C₅H₁₂NO₄P
• Molecular Weight: 181.13
• Mol File: 35597-44-5.mol
• Article Data: 28

Chemical Properties

• Melting Point: 209-210 °C
• Boiling Point: 519.1°C at 760 mmHg
• Flash Point: 267.7°C
• Appearance: /
• Density: 1.378g/cm³
• Vapor Pressure: 3.61E-12mmHg at 25°C
• Refractive Index: 1.5
• PKA: 2.22±0.10(Predicted)
• CAS DataBase Reference: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)-(35597-44-5)
• EPA Substance Registry System: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)-(35597-44-5)

Safety Data

• Hazardous Substances Data: 35597-44-5(Hazardous Substances Data)

Usage

Chemical Properties

A 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid that has S configuration at position 2. A glutamine synthetase inhibitor, it is used (generally as the corresponding ammonium or sodium salts, known as glufosinate-P-ammonium and glufosinate-P-sodium, respectively) as a herbicide to control annual weeds and grasses.

InChI:InChI=1/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)/t4-/m0/s1

Upstream product

• 128574-46-9 (S)-2-Amino-4-(ethoxy-methyl-phosphinoyl)-butyric acid 
• 73777-49-8 L-homoalanine-4-yl(methyl)phosphinic acid hydrochloride 
• 51276-47-2 DL-homoalanin-4-yl(methyl)phosphinic acid 
• 79778-02-2 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid 
• 56-86-0 L-glutamic acid 
• 85178-62-7 L-Desmethylphosphinothricin 

Relevant articles and documents

AN EFFICIENT ASYMMETRIC SYNTHESIS OF BOTH ENANTIOMERS OF PHOSPHINOTHRICIN

An efficient synthesis of both enantiomers of phosphinothricin 1 by alkylation of metalated chiral bis-lactim ethers is described.

Efficient racemization of N-phenylacetyl-D-glufosinate for L-glufosinate production

Most amino acids contain chiral centres and exist as both D-enantiomer and L-enantiomer. The optically pure enantiomer is often more valuable than the racemate. Enzymatic resolution provides an effective strategy to obtain optically pure amino acids but often results in large amounts of unwanted isomer. In this study, optically pure L-glufosinate (L-PPT) was obtained by coupling amidase-mediated hydrolysis of N-phenylacetyl-D,L-glufosinate with racemization of N-phenylacetyl-D-glufosinate (NPDG), which exclusively exhibits effective herbicidal properties compared with its D-enantiomer. To improve the yield of L-PPT, the racemization reaction conditions were optimized, and through single-factor experiments, the optimal reaction temperature, reaction time, and mole ratio of phenylacetic acid to NPDG were determined to be 150°C, 30?minutes, and 1.5, respectively. The response surface methodology was applied to further optimize the racemization conditions, and the final yield of L-PPT reached 96.13% with optimum reaction temperature of 154°C, reaction time of 23?minutes, and phenylacetic acid/NPDG mole ratio of 1.7, respectively. Moreover, adding a small amount of acetic anhydride further raised the yield of L-PPT to 97.02%.

L-GLUFOSINATE INTERMEDIATE AND L-GLUFOSINATE PREPARATION METHOD

Provided are L-glufosinate intermediate preparation method or L-glufosinate preparation method, the method, for preparing L-glufosinate intermediate or L-glufosinate from an L-homoserine derivative, comprising a step of preparing a compound of Chemical Formula 2 from a compound of Chemical Formula 1.

Development of a biocatalytic cascade for synthesis of 2-oxo-4-(hydroxymethylphosphinyl) butyric acid in one pot

2-Oxo-4-(hydroxymethylphosphinyl) butyric acid (PPO) is an important precursor compound for the broad-spectrum herbicide l-glufosinate (L-PPT). In this study, the gene of d-amino acid oxidase (DAAO) was cloned and expressed in Escherichia coli. By coupling exogenous catalase (CAT), a biocatalytic cascade was constructed for synthesis of PPO in one pot. The bioprocess was optimized on a 300 mL scale reaction by one factor at a time optimization. The conversion of this biocatalytic cascade achieved 46.8% towards 400 mM DL-PPT within 4 h. These results indicated that DAAO could be applied to the large-scale bioproduction of PPO and provide a promising route for the asymmetric synthesis of L-PPT by bio-enzymatic methods using PPO as the substrate.