51276-47-2

Basic information

• Product Name: 2-amino-4-(hydroxymethylphosphinyl)butyric acid
• Synonyms: 2-amino-4-(hydroxymethylphosphinyl)butyric acid;Phosphinothricin;Phosphinothricin ammonium salt;2-Amino-4-(methylhydroxyphosphinyl)butyric acid;HOE-35956;HOE-866;C05042;IAJOBQBIJHVGMQ-UHFFFAOYSA-N
• CAS NO: 51276-47-2
• Molecular Formula: C₅H₁₂NO₄P
• Molecular Weight: 181.126841
• EINECS: 257-102-5
• Mol File: 51276-47-2.mol

Chemical Properties

• Melting Point: 229-231° (dec)
• Boiling Point: 519.1 ºC at 760 mmHg
• Flash Point: 267.7 ºC
• Appearance: /
• Density: 1.378 g/cm³
• Vapor Pressure: 3.61E-12mmHg at 25°C
• Refractive Index: 1.5
• PKA: 2.22±0.10(Predicted)
• CAS DataBase Reference: 2-amino-4-(hydroxymethylphosphinyl)butyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-4-(hydroxymethylphosphinyl)butyric acid(51276-47-2)
• EPA Substance Registry System: 2-amino-4-(hydroxymethylphosphinyl)butyric acid(51276-47-2)

Safety Data

• Hazardous Substances Data: 51276-47-2(Hazardous Substances Data)

Usage

Enzyme inhibitor

This dephospho transition-state analogue (FW = 177.10 g/mol; CAS 51276- 47-2) is naturally occurring glutamate analogue, first isolated from Streptomyces viridochromogenes. Phosphonothricin is a slow, tight-binding inhibitor of glutamine synthetase that binds at the glutamate binding site and stabilizes the flap of a glutamyl residue in a position blocking glutamate entry into the active site, thereby trapping the inhibitor on the enzyme. Phosphinothricin undergoes an ATP-dependent phosphorylation. Note: Phosphinothricin is a component of the antibiotics bialaphos and phosalacine. The monoammonium salt of the racemic compound, also called glufosinate-ammonium, is a post-emergent herbicide.

Metabolic pathway

When 14C-phosphinothricin [homoalanin-4-yl- (methyl)phosphinic acid] is incubated in the cell suspension cultures of soybean, wheat, and maize, in maize cells which take up to 50% of the applied radioactivity, four different metabolites are detected which are identified as 4-methylphosphinico-2-oxo- butyric acid, 4-methylphosphinico-2-hydroxybutyric acid, 4-methylphosphinicobutyric acid, and 3- methylphosphinicopropionic acid. In soybean and wheat cultures, 10 and 6% of the applied radioactivity is taken up, respectively. In soybean, only one metabolite, 3-methylphosphinicopropionic acid, is detected, whereas in wheat, 4-methyl- phosphinicobutyric acid is additionally present.

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)

Upstream product

• 74-90-8 hydrogen cyanide 
• 59374-45-7 (3,3-Dimethoxy-propyl)-methyl-phosphinic acid ethyl ester 
• 15715-41-0 methyldiethoxyphosphine 
• 73385-92-9 ethyl methyl-(3,3-diethoxypropyl)phosphinate 
• 151-50-8 potassium cyanide 
• 36120-72-6 methyl-vinyl-phosphinic acid 2-chloro-ethyl ester 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 40682-54-0 ethyl N-benzylideneglycinate 
• 63314-88-5 vinylmethylphosphinic acid methyl ester 
• 139574-94-0 methyl 2-(benzylideneamino)-4-(methoxymethylphosphinyl)butyrate 
• 139574-95-1 2-{[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-amino}-4-(methoxy-methyl-phosphinoyl)-butyric acid methyl ester 
• 139575-01-2 2-{[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-4-(methoxy-methyl-phosphinoyl)-butyric acid methyl ester 
• 87647-63-0 4-(Methoxy-methyl-phosphinoyl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-butyric acid ethyl ester 
• 109541-73-3 METHYL DL-2-(1,3-DIHYDRO-1,3-DIOXO-2H-ISOINDOL-2-YL)-4-(ETHOXYMETHYLPHOSPHINYL)BUTANOATE 

Downstream Products

• 77182-82-2 ammonium glufosinate 
• 77182-82-2 2-amino-4-(hydroxymethylphosphinyl)butyric acid monoammonium salt 
• 82785-28-2 4-[hydroxy(methyl)phosphonyl]-DL-homoalanine 
• 15090-23-0 2-carboxyethyl-methyl-phosphinic acid 
• 79778-02-2 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid 
• 35597-44-5 L-phosphinothricin 
• 328-50-7 α-ketoglutaric acid 

Relevant articles and documents

Preparation method of glufosinate-ammonium

The invention discloses a preparation method of glufosinate-ammonium. The preparation method comprises the following steps that 1, in alkaline environment, 4-(hydroxymethyl phosphono)-2-carbonyl butyric acid (I) and a benzylamine solution react to produce 2-[( phenyl amino)-4-(methyl sodium phosphate)-sodium butyrate (II); 2, 2-[(phenyl amino)-4-(methyl sodium phosphate)-sodium butyrate (II) is subjected to acid hydrolysis to obtain glufosinate-ammonium (III). Compared with the prior art, the preparation method has the advantages that the conditions are mild; the yield of the glufosinate-ammonium is high; the purity is high.

Glufosinate ammonium preparation method

The invention relates to a glufosinate ammonium preparation method. According to the present invention, nitro is introduced by using a simple and economical method, and is reduced under a mild condition so as to introduce amino group as the key step, such that the method for introducing amino by using other expensive amino acid derivatives or other toxic nitrogen-containing compounds is avoided, and the amino protection and deprotection during the reaction is eliminated; and the preparation method has advantages of simple reaction process, mild condition, simple and easily-available raw materials, simple operation and good atom economy, and is extremely suitable for industrial production.

Process for preparing glufosinate acid with hydrogenation method

The invention discloses a process for preparing precursor glufosinate acid of glufosinate acid with a catalytic hydrogenation method. The process comprises the following steps: firstly, reacting N-ethyl acetamidomalonate with 2-[ethyoxyl(methyl)phosphonyl] acetaldehyde under the actions of an acid binding agent and a dehydrating agent to generate an intermediate, namely, 2-acetamido-4-[ethyoxyl(methyl)phosphonyl]butyl-2-olefine acid ester; secondly, separating and purifying the intermediate, performing hydrogenation by taking ethanol as a solvent under the catalytic action of a hydrogenation catalyst to obtain a product, namely, 2-acetamido-4-[ethyoxyl(methyl)phosphonyl]ethyl butyrate, wherein the two-step yield can be 85 percent or more; lastly, performing deprotection with concentrated hydrochloric acid, and removing the hydrochloric acid to obtain the glufosinate acid. The process has the advantages of easiness in reaction and post-treatment operation, high yield, recyclability of the hydrogenation catalyst and the like, and has a very wide industrial prospect.

A aminonitrile preparation method and process for the preparation of the intermediates of glufosinate

The invention discloses a preparation method of amino-nitrile and an intermediate for preparing glufosinate-ammonium. The preparation method disclosed by the invention aims at solving the problem of low glufosinate-ammonium yield by using acetal in the existing methods. Different from the existing methods for preparing glufosinate-ammonium, the method disclosed by the invention comprises the following steps: firstly reacting acetal with acetylchloride to obtain an enol ether intermediate, reacting the enol ether intermediate with sodium cyanide to obtain amino-nitrile, and finally hydrolyzing the amino-nitrile to obtain the glufosinate-ammonium. The method has the advantages of higher reaction yield and capacity of remarkably reducing the production cost of the glufosinate-ammonium.

LJ reaction in the preparation wittich reagent and application of glufosinate in

The present invention relates to an application of a new LJ intramolecular isomerization reaction in preparation of a wittig reagent and a herbicide of glufosinate-ammonium. With the application, a new approach of a synthesis route for preparing the wittig reagent and the glufosinate-ammonium is developed, the disadvantages of the existing wittig reaction are improved, and the industrial design of the glufosinate-ammonium production is improved.

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.

A kind of preparation method for treating keratoconjunctival and wherein the intermediate preparation method

The invention relates to the technical field of pesticides and particularly relates to a method for preparing glufosinate-ammonium and a preparation method for an intermediate thereof. The method is characterized by comprising the following steps of: taking phosphorus trichloride and phosphite ester as raw materials, preparing chlorophosphite ester under the catalysis of the mixture of triethylamine, N,N-dimethylformamide or pyridine and hexamethylphosphoramide, preparing methylmagnesium chloride from chloromethane and magnesium metal, preparing methyl phosphite ester by reacting the chlorophosphite ester with methylmagnesium chloride, carrying out an addition reaction on the methyl phosphite ester and acrolein, carrying out a Strecker reaction on the product of the addition reaction, sodium cyanide, ammonium chloride and ammonia water under the catalysis of montmorillonite-supported lewis acid, and carrying out hydrolyzing and purifying after finishing the Strecker reaction, so as to obtain the high-purity glufosinate-ammonium. The method provided by the invention has the advantages that side reactions are few, products are high in purity and easy to separate, and catalysts and solvents are easy to obtain, regenerate and recycle; and the production cost is lowered, and the method is accordant with the trend of green chemical industry and is suitable for industrial production.

Grass amine phosphine method for the preparation of

The invention discloses a Glufosinate-ammonium and its derivative improved preparation method, the method comprises the following steps: diethyl methyl-phoshphonite, acraldehyde and acetic anhydride are subjected to an addition reaction, a reactant, sodium cyanide (editpotassium cyanide for replacing) and an ammonia water solution of ammonium chloride are subjected to an improved STRECKER reaction without separation, the product is subjected to hydrolysis and ammonification for forming salt to obtain Glufosinate-ammonium. The preparation method has the characteristics of high selectivity and high yield.

Grass ammonium phosphine method for the preparation of

The invention belongs to the field of chemical synthesis, and particularly relates to a new preparation method of a glufosinate-ammonium weed killer. The preparation method is characterized in that methyl phosphorus dichloride reacts with alcohol so as to prepare a methyl phosphonate compound IV, and then the methyl phosphonate compound IV reacts with acrolein so as to prepare a methyl propionaldehyde phosphonate compound II; the methyl propionaldehyde phosphonate compound II is subjected to Bucherer-Bergs ring-closure reaction so as to prepare a hydantoin derivative shown in a formula III, and the hydantoin derivative is subjected to hydrolysis reaction so as to prepare the glufosinate-ammonium compound shown in a formula I. The preparation method of the glufosinate-ammonium has the advantages that required conditions are mild, the detection is easy, the required raw materials are easily available and low in cost, the yield of the obtained product is high, the obtained product has high purity, and ammonium salt is removed without needing recrystallization over and over again.

Purification method of glufosinate

The invention relates to a purification method of glufosinate. The method comprises the following steps: adding a glufosinate hydrochloride crude product into a solvent, adding amino acid and an aqueous solution of alkali, reacting for 0.5-1.5 h, adjusting pH of the reaction system to 1-7, filtering and drying to obtain glufosinate-ammonium acid; and dissolving glufosinate-ammonium acid in a solvent, introducing ammonia gas and carrying out a salt-forming reaction, precipitating a glufosinate solid, filtering and drying to obtain high-purity glufosinate. According to the purification technology, use of fatty amine which is hard to remove and high-risk oxirane and epoxypropane is avoided. The steps are simple. The obtained glufosinate has low content of inorganic salt, high purity, high yield and high safety. In addition, water or alcohol is used as a solvent in the technological process, and a neutralization reaction is carried out by the use of ammonia water and inorganic base. The purification method accords with the ecology and economy principle, and has a good industrial prospect. In addition, purification is carried out by addition of amino acid, and purification efficiency and product purity are higher.