15090-23-0

Basic information

• Product Name: 3-METHYLPHOSPHINICOPROPIONIC ACID
• Synonyms: Propionic acid, 3-(hydroxymethylphosphinyl)-;3-METHYLPHOSPHINICOPROPIONIC ACID;3-(hydroxymethylphosphinoyl)propionic acid;3-METHYLPHSOPHINICOPROPIONIC ACID PESTAN;3-Methylphosphinylpropionic Acid;3-(METHYLPHOSPHINICO)PROPIONIC ACID STANDARD;3-(Hydroxymethylphosphinyl)propionic acid;Einecs 239-144-6
• CAS NO: 15090-23-0
• Molecular Formula: C₄H₉O₄P
• Molecular Weight: 152.09
• EINECS: 239-144-6
• Product Categories: Metabolites & Impurities;Phosphorylating and Phosphitylating Agents;Isotope Labelled Compounds;Metabolites & Impurities, Phosphorylating and Phosphitylating Agents;META - METH;Alpha sort;H-MAlphabetic;M;Pesticides&Metabolites
• Mol File: 15090-23-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: approximate 95℃ (dec.)
• Boiling Point: 488.609 °C at 760 mmHg
• Flash Point: 249.302 °C
• Appearance: /
• Density: 1.372 g/cm³
• Vapor Pressure: 6.95E-11mmHg at 25°C
• Refractive Index: 1.463
• Storage Temp.: 2-8°C
• PKA: 2.69±0.50(Predicted)
• BRN: 2242347
• CAS DataBase Reference: 3-METHYLPHOSPHINICOPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLPHOSPHINICOPROPIONIC ACID(15090-23-0)
• EPA Substance Registry System: 3-METHYLPHOSPHINICOPROPIONIC ACID(15090-23-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 15090-23-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYLPHOSPHINICOPROPIONIC ACID is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique chemical structure allows it to be a key component in the development of new drugs and therapies.
Used in Chemical Synthesis:
3-METHYLPHOSPHINICOPROPIONIC ACID is used as a building block in the synthesis of complex organic molecules. Its phosphinic acid group provides a versatile platform for further chemical reactions, making it a valuable asset in the field of organic chemistry.
Used in Metabolite Research:
3-METHYLPHOSPHINICOPROPIONIC ACID is used as a major labelled metabolite of Glufosinate (G596950). This application aids in the study of the metabolic pathways and the effects of Glufosinate on various biological systems.
Used in Agricultural Industry:
As the major metabolite of Glufosinate, 3-METHYLPHOSPHINICOPROPIONIC ACID plays a role in the agricultural industry, particularly in the development and understanding of herbicides and their impact on crops and the environment.

InChI:InChI=1/C4H9O4P/c1-9(7,8)3-2-4(5)6/h2-3H2,1H3,(H,5,6)(H,7,8)

Upstream product

• 15090-24-1 3-(methylchlorophosphoryl)propionyl chloride 
• 212136-81-7 bis(trimethylsilyl) 2-(methoxycarbonyl)ethylmethylphosphonite 
• 74-88-4 methyl iodide 
• 15090-26-3 methyl 3-(methoxy-methylphosphinyl)propionate 
• 15090-27-4 ethyl 3-(ethoxymethylphosphinyl)propionate 
• 51276-47-2 DL-homoalanin-4-yl(methyl)phosphinic acid 
• 676-97-1 methylphosphonic acid dichloroanhydride 
• 79-10-7 acrylic acid 
• 15171-48-9 2-methyl-2,5-dioxo-1,2-oxaphospholane 
• 168900-56-9 trimethylsilyl methyl(3-trimethylsiloxy-3-cyano-2-propenyl)phosphinate 

Relevant articles and documents

Synthesis and performance of star-shaped aluminum phosphinate flame retardant

A star-shaped aluminum dimethyl(2,2-dimethyl-1,3-propylene)bis(oxy)bicarbonylethyldiphos phinate (AlCP) was synthesized by esterifying reaction between 2-methy-2,5-dioxo-1,2-oxaphospholane (OP) and neopentyl glycol following by neutralizing with aluminum hydroxide. The structure and composition were confirmed with FTIR, 1H NMR, 31P NMR and X-ray fluorescent spectroscopy. AlCP begins to decompose at 370?°C, matching the initial decomposition temperature of PBT. It endows PBT with desired flame retardancy and anti-dripping property and shows good compatibility with PBT. When the total filler loading is kept at 17, 15–13?mass% AlCP combining with 2–4?mass% MC can make the PBT passing the UL 94 V0 rating and eliminating dripping. In addition, the AlCP has a little influence on the mechanical properties of PBT. The tensile strength and notched impact strength of PBT containing 17?mass% AlCP only reduce by 5.6 and 4?%, respectively, comparing to the pure PBT. The SEM photographs show that AlCP has a good compatibility with PBT. Microcombustion calorimeter, TG-FTIR and SEM results show that AlCP can depress the heating release and promote char forming during combustion and acts mainly in the condensed phase.

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.

Interaction of 2-methyl-2,5-dioxo-1,2-oxaphospholane with trimethylsilyl cyanide

The reaction of 2-methyl-2,5-dioxo-1,2-oxaphospholane (1) with trimethylsilyl cyanide was found to give, depending on conditions, three organophosphorus compounds: trimethylsilyl methyl(2-cyanocarbonylethyl)phosphinate (2), trimethylsilyl methyl(3-trimethylsiloxy-3,3-dicyanopropyl)phosphinate (3) and trimethylsilyl methyl(3-trimethyl-siloxy-3-cyano-2-propenyl)phosphinate (4).On hydrolysis of 3 under mild conitions, methyl(3-hydroxy-3,3dicarboxypropyl)phosphinic acid (7) was obtained.The latter is readily decarboxylated on heating to give methyl(3-hydroxy-3-carboxy-propyl)phosphinic acid (8).The interaction of 2 and 4 with water or alcohols gives, correspondingly, methylphosphinic acids (11-13).Methyl(2-oxamoylethyl)phosphinic acid (14) was prepared by successive treatment of propenylphosphinate 4 with HCl gas and water.

Lithium salt compound, preparation method thereof and lithium ion battery electrolyte containing lithium salt compound

The invention provides a preparation method of a lithium salt compound, which comprises the following steps: adding alkylphosphite dialkyl ester into a protic solvent, uniformly mixing, and adding alkyl acrylate while stirring to react, thereby obtaining a compound A; adding an acid solution A into the compound A, carrying out a heating reflux reaction, adding acetone after the reaction is completed, and crystallizing to obtain a compound B; adding an alcoholic solution and an acid solution B into the compound B for esterification to obtain a compound C; adding an alcoholic solution into the compound C, uniformly stirring, then adding a lithium source, stirring for reaction, and concentrating and crystallizing after the reaction is finished, so as to obtain the lithium salt compound. The invention also provides a lithium ion battery electrolyte containing the lithium salt compound. The lithium salt compound prepared by the method provided by the invention has flame retardance and goodconductivity, and the lithium ion battery electrolyte composed of the lithium salt compound is stable in performance, safe and reliable.

Preparation method of 2-carboxyethyl methyl phosphinic acid

The invention discloses a preparation method of 2-carboxyethyl methyl phosphinic acid and belongs to the technical field of organic synthesis. The invention aims to provide the preparation method of 2-carboxyethyl methyl phosphinic acid, which is simple in operation, few in byproduct, high in yield and low in cost. The preparation method of 2-carboxyethyl methyl phosphinic acid comprises the following steps: performing reaction on methylphosphoric dichloride and acrylic acid, adding water after reaction, enabling the system to react in a mixed solution of water and an organic solvent, and obtaining 2-carboxyethyl methyl phosphinic acid after reaction. By the method, 2-carboxyethyl methyl phosphinic acid is prepared by a one-pot method efficiently, an intermediate does not need to be separated, the method is simple and safe in operation, the byproducts are few, the yield is high, the purity is high, the production cost of 2-carboxyethyl methyl phosphinic acid is obviously reduced and industrialized production is facilitated.

Single molecular expansion type alkyl phosphinate flame retardant and preparation method thereof

The invention discloses a single molecular expansion type alkyl phosphinate flame retardant. A structural general formula is shown in the description, a molecular structure is starlike, R-O- is a hydroxyl dehydrogenized structure after a nitrogen-containing polyhydroxy compound is subjected to esterification reaction, the formula (shown in the description) is a hydroxyl removed structure provided with molecular hydroxyl and obtained after organic phosphonic acid esterification reaction, n corresponds to the number of hydroxy and amidogen of the nitrogen-containing polyhydroxy compound, and M is a metal or semi-metal having the valence m. The invention further discloses a preparation method the flame retardant. The three-source proportion of the flame retardant can be regulated and controlled by selecting different nitrogen-containing polyhydroxy compounds. The molecular structure contains P-C keys and has excellent heat stability and good chemical properties. A specific carboxylic ester structure has good mixing compatibility with a polymer, and the original mechanical properties of the polymer can be retained to the greater degree. Metal ions in molecules can prevent the flame retardant from migrating from the polymer and meanwhile have a catalytic charing effect.

4 - (hydroxy-(methyl) phosphinyl) - 2-oxo-butyric acid production process

The invention discloses a preparation method of 4-(hydroxy-(methyl)phosphinyl)-2-oxobutyric acid. The preparation method comprises following steps: synthesis of methylphosphoric dichloride; recovery of diethyl phthalate, synthesis of methyl chloro phosphinic propionyl chloride; synthesis of methoxyl methyl phosphinic methyl propionate; synthesis of 4-(hydroxy-(methyl)phosphinyl)-2-oxobutyric acid; and post treatment. Technology processes of the preparation method are simple; yield is high; production cost is low; and production technology is clean. In addition, when 4-(hydroxy-(methyl)phosphinyl)-2-oxobutyric acid obtained by the preparation method is used for synthesis of weed killer glufosinate-ammonium, levo glufosinate-ammonium with high weed killing function is obtained, so that weed killing effect of glufosinate-ammonium is improved greatly.

Synthesis of Phosphinic Acids from Hypophosphites. I. Acrylates as an Unsaturated Component

A method is developed for preparing asymmetric phosphinic acids from hypophosphites and α,β-unsaturated carboxy compounds. A series of new functionally substituted phosphinic acids are prepared.