589-57-1

Basic information

• Product Name: DIETHYL CHLOROPHOSPHITE
• Synonyms: AURORA KA-1221;DIETHYL CHLOROPHOSPHITE;DIETHYL CHLOROPHOSPHONITE;DIETHYL PHOSPHOROCHLORIDITE;ETHYL PHOSPHOROCHLORIDITE;Chlorodiethoxyphosphine;Chlorodiethyl phosphite;Diethyl chloridophosphite
• CAS NO: 589-57-1
• Molecular Formula: C₄H₁₀ClO₂P
• Molecular Weight: 156.55
• EINECS: 209-652-2
• Product Categories: Phosphorus Halides;Building Blocks;Chemical Synthesis;Organic Building Blocks;Phosphorus Compounds
• Mol File: 589-57-1.mol

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 153-155 °C(lit.)
• Flash Point: 34 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.089 g/mL at 20 °C(lit.)
• Vapor Pressure: 4.17mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in DMSO and chloroform. Reacts with water.
• Sensitive: Moisture Sensitive
• Merck: 14,3841
• BRN: 1098392
• CAS DataBase Reference: DIETHYL CHLOROPHOSPHITE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL CHLOROPHOSPHITE(589-57-1)
• EPA Substance Registry System: DIETHYL CHLOROPHOSPHITE(589-57-1)

Safety Data

• Hazard Codes: F,C
• Statements: 11-14-34-37
• Safety Statements: 16-26-36/37/39-45-7/8
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 589-57-1(Hazardous Substances Data)

Usage

Uses

1. Used in the Synthesis of Organophosphates:
DIETHYL CHLOROPHOSPHITE is used as a key intermediate for the synthesis of organophosphates, which are essential compounds in various applications, including pharmaceuticals and agrochemicals. These organophosphates are considered anticholinesterase agents, as observed in studies.
2. Used in Peptide Synthesis:
In the field of peptide chemistry, DIETHYL CHLOROPHOSPHITE serves as a valuable reagent for the synthesis of peptides. Its ability to act as a phosphorylating agent allows for the formation of peptide bonds, which are crucial for the structure and function of proteins.
3. Used as a Phosphorylating Agent:
DIETHYL CHLOROPHOSPHITE is used as a versatile phosphorylating agent for ester and lactone enolates, amines, and alkenols. This property makes it a valuable tool in the synthesis of a wide range of organic compounds, including those with potential applications in pharmaceuticals, materials science, and other industries.
4. Used in Pharmaceutical Industry:
DIETHYL CHLOROPHOSPHITE is used as a building block for the development of new pharmaceutical compounds, particularly those with anticholinesterase activity. These compounds have potential applications in the treatment of various neurological disorders, such as Alzheimer's disease and myasthenia gravis.
5. Used in Agrochemical Industry:
In the agrochemical industry, DIETHYL CHLOROPHOSPHITE is used in the synthesis of organophosphate-based pesticides. These pesticides are effective in controlling pests and protecting crops, contributing to increased agricultural productivity.
6. Used in Materials Science:
DIETHYL CHLOROPHOSPHITE is also utilized in the development of new materials with unique properties, such as self-healing materials and advanced polymers. Its role as a phosphorylating agent allows for the creation of novel structures and functionalities in these materials.

InChI:InChI=1/C4H10ClO2P/c1-3-6-8(5)7-4-2/h3-4H2,1-2H3

Upstream product

• 56-23-5 tetrachloromethane 
• 21646-99-1 diphosphorous acid tetraethyl ester 
• 1498-42-6 phosphorodichloridous acid ethyl ester 
• 141968-97-0 1,3-Dibutyl-2-ethoxy-4,5-dimethyl-2,3-dihydro-1H-[1,3,2]diazaphosphole 
• 78-10-4 tetraethoxy orthosilicate 
• 7719-12-2 phosphorus trichloride 
• 122-52-1 triethyl phosphite 
• 2524-04-1 diethyl phosphorochloridothioate 
• 115-80-0 Triethyl orthopropionate 
• 762-04-9 Diethyl phosphonate 
• 126199-84-6 2-ethoxy-5-methyl-1,3,2-oxathiaphospholene 
• 999-01-9 O,O'-diethyl thiophosphonate 
• 18611-22-8 N-diethoxyphosphinoyltrifluoroacetimidoyl chloride 
• 79948-06-4 O,O-diethyl-N-butyl-N-isobutenyl aminophosphite 

Downstream Products

• 18359-24-5 phosphorous acid diethyl ester-(2-chloro-ethyl ester) 
• 35112-45-9 phosphorous acid ethyl ester bis-(2-chloro-ethyl) ester 
• 122-52-1 triethyl phosphite 
• 688-49-3 ethyl (diethoxyphosphino)acetate 
• 66628-81-7 diethoxyphosphine 
• 58825-45-9 2-ethoxy-2,3-dihydro-1H-1,3,2-benzodiazaphosphole 
• 5524-65-2 O,O-Diaethyl-N-<4-brom-phenyl>-amidophosphorigsaeure 
• 19820-97-4 Selenophosphoric acid O-ethyl ester O'-methyl ester Se-phenyl ester 
• 116016-89-8 O,O-diethyl O-<1-phenyl-2-(5-phenyl-2-pyrimidinyl)vinyl>phosphorothioate 

Relevant articles and documents

Phosphine ligand compound and preparation method thereof, catalyst composition and application thereof and vinyl acetate hydroformylation method (by machine translation)

The invention relates to the field of vinyl acetate hydroformylation, and discloses a phosphine ligand compound and a preparation method thereof, a catalyst composition and application of the phosphine ligand compound and vinyl acetate hydroformylation. The phosphine ligand compound has the structure shown in formula (1); wherein A is selected from substituted or unsubstituted phenyl; R1 , R2 , R3 And R4 C is each independently selected from substituted or unsubstituted C1 - C20 Alkyl, substituted or unsubstituted phenyl; A, R1 , R2 , R3 And R4 The optionally present substituents are each independently selected from C. 1 - C20 Alkyl, halogen and C1 - C10 The phosphorus ligand compound provided by the invention can effectively improve the vinyl acetate conversion rate and 2 - acetoxy propionaldehyde selectivity. (by machine translation)

CHEMOSELECTIVE THIOL-CONJUGATION WITH ALKENE OR ALKYNE-PHOSPHONAMIDATES

Disclosed are novel conjugates and processes for the preparation thereof. A process for the preparation of alkene- or alkyne-phosphonamidates comprises the steps of (I) reacting a compound of formula (III), with an azide of formula (IV), to prepare a compound of formula (V), reacting a compound of formula (V) with a thiol-containing molecule of formula (VI), resulting in a compound of formula (VII).

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.

Synthetic method of methyl phosphite and glufosinate-ammonium

The invention discloses a synthetic method of methyl phosphite and glufosinate-ammonium. The method comprises the steps: with phosphorus pentasulfide as a starting material, then carrying out vulcanization reaction, chlorination reaction, water washing and distillation purification, then carrying out catalytic hydrogenation to obtain chloride phosphite (III), and next carrying out Grignard reaction to obtain methyl phosphite (IV), wherein R is C1-C4 alkyl. The method comprises the steps: with phosphorus pentasulfide as the starting material, then carrying out vulcanization reaction, chlorination reaction, water washing and distillation purification, then carrying out catalytic hydrogenation to obtain chloride phosphite, next carrying out Grignard reaction to synthesize methyl phosphite (IV), and thus obtaining the final product glufosinate-ammonium through a Strecker route of the prior art. The synthetic yield is increased, methyl phosphorus dichloride and other unstable corrosive intermediates cannot be produced, the discharge of three-waste substances is reduced, and environment-friendly costs and pressure are reduced.

Revisiting the phospha-Wittig-Horner reaction

P,P-Dichlorophosphines 2a-c (RPCl2, R = Ph (a), t-Bu (b), 2,4,6-Me3Ph (c)) and P,P-dibromophosphines 4d,e (RPBr2, R = (i-Pr)3SiC≡C (d) and H2C=CH (e)) react with triethylphosphite under Michaelis-Arbuzov conditions to give phosphinodiphosphonates 3a-e in quantitative yields. After complexation to W(CO)5 and treatment with CH3ONa, phospha-Wittig-Horner reagents 9a,b are obtained on a multigram scale in good overall yield. Phospha-Wittig-Horner reagents with unsaturated substituents at IIIP (10d,e) can be prepared in analogous procedures; however, they prevail in an unusual ylide form that allows conjugation between the lone pair and the acetylene and vinyl π-systems, respectively. Phosphinophosphonate 9a has been characterized by X-ray crystallography and is shown to react smoothly with acetone within minutes. The resulting W(CO)5-coordinated phosphaalkene is shown to dimerize to a 1,2-diphosphitane or to undergo a 1,3-proton shift depending on the reaction conditions. In addition, a one-pot synthetic sequence starting from W(CO)5-coordinated phosphinodiphosphonates 5d,e has been developed to engage compounds with vinyl and acetylene substituents in phospha-Wittig-Horner reactions.

PROCESS FOR PRODUCING HIGH-PURITY CHLOROPHOSPHITE

There is provided a process capable of preventing the adhesion of a catalyst to an evaporator in a step of separating a chlorophosphite as a target substance from a reaction liquid by evaporation. The process includes a first step of allowing phosphorus trichloride and a phosphorous acid triester represented by (RO)3P to react in the presence of a catalyst having a viscosity at 80° C. of 100 mPa·s or lower to produce a chlorophosphite represented by RO(R′)PCl, and a second step of vaporizing a reaction liquid containing the chlorophosphite obtained in the first step, in a short time, to separate the catalyst.

Selective synthesis of organophosphites

Disclosed herein is a process for the selective synthesis of triorganophosphites intermediates, including chloridites and dichloridites, from PX3 (X=Cl, Br or I), alcoholos and triorganoamines where alcohol and triorganoamine are added either (a) separately and concurrently, or (b) alternating equimolar portions of amine and alcohol.

The study of phosphoramidite as O-phosphitylation agent and its reactivity

O-phosphorylated peptide and amino acid are important in living system. In this paper, Dialkyl-N,N-dialkyl phosphoramidites (DDPA) 3 were synthesized using two methods. The reaction of DDPA with the hydroxyl group of the corresponding amino acids in the presence of tetrazole, followed by oxidation, gave O-phosphoryl amino acid methyl esters in a good yield. A systematical study of the reactivity of DDPA was presented too.

Reaction of Phosphorus Acids with Nitriles

Reaction of dialkyl hydrogen phosphates, dialkyl hydrogen phosphorothioates and dialkyl hydrogen dithiophosphates with acetonitrile and benzonitrile is studied by 1H and 31P spectroscopy. O,O-Dimethyl and O,O-bis(1,1,2-trihydroperfluoropropyl) hydrogen thiophosphates exhibit increased reactiovoty toward nitriles as compared with O,O-diethyl hydrogen dithiophosphate.

Reaction of (chloromethyl)phosphonic(-phosphinic) chlorides with silylated protic nucleophiles

Reactions of (chloromethyl)phosphonic(-hosphinic) chlorides with trimethylalkoxy(-phenoxy, -dialkylamino)silanes are accompanied by elimination of trimethylchlorosilane and lead to formation of related substitution products. Reactions of bis(chloromethyl)phosphinic chloride and (chloromethyl)phosphinic dichloride with neutral and hydrogen silyl phosphites were studied. The reactions of bis(chloromethyl)phosphinic chloride with tris(trimethylsilyl)phosphite, diethyl trimethylsilyl phosphite, and bis(trimethylsilyl) hydrogen phosphite yield trimethylsilyl bis(chloromethyl)phosphinate. Similar reactions with (chloromethyl)phosphonic dichloride resulted in isolation of bis(trimethylsilyl) (chloromethyl)phosphonate.