676-98-2

Usage

Uses

Used in Chemical Synthesis:
METHYLPHOSPHONOTHIOIC DICHLORIDE is used as a reagent for the synthesis of various organic compounds. Its application is due to its ability to react with a wide range of substrates, facilitating the formation of new chemical bonds and functional groups.
Used in Pharmaceutical Industry:
METHYLPHOSPHONOTHIOIC DICHLORIDE is used as an intermediate in the production of pharmaceuticals. It is chosen for this application because of its reactivity and the potential to form various drug molecules with desired therapeutic properties.
Used in Agrochemical Industry:
METHYLPHOSPHONOTHIOIC DICHLORIDE is used as a building block for the development of agrochemicals, such as pesticides and herbicides. Its application in this industry is due to its ability to form stable and effective compounds that can protect crops from pests and enhance agricultural productivity.
Used in Material Science:
METHYLPHOSPHONOTHIOIC DICHLORIDE is used as a precursor in the development of new materials with specific properties, such as improved thermal stability or chemical resistance. Its application in material science is driven by its potential to create novel materials with enhanced performance characteristics.

Air & Water Reactions

Reacts with water to form hydrochloric acid, reaction may be violent.

Reactivity Profile

METHYL PHOSPHONOTHIOIC DICHLORIDE is water reactive. Incompatible with strong oxidizing agents, alcohols, bases( including amines). May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Health Hazard

Inhalation causes irritation of nose and throat; effects are quite similar to those of phosgene. Ingestion causes irritation of mouth and stomach. Delayed, painful eye irritation may occur from exposure to vapor; liquid causes severe irritation. Contact with skin causes irritation and burns.

Fire Hazard

Special Hazards of Combustion Products: Irritating hydrogen chloride, sulfur dioxide and other fumes may be formed in fire.

Safety Profile

A corrosive irritant to skin, eyes, and mucous membranes. When heated to decomposition it emits very toxic fumes of Cl-, POx, and SOx.

InChI:InChI=1/CH3Cl2PS/c1-4(2,3)5/h1H3

Upstream product

• 676-97-1 methylphosphonic acid dichloroanhydride 
• 676-83-5 methyldichlorophosphane 

Downstream Products

• 13789-63-4 methyl-thiophosphonic acid-dianilide 
• 18005-38-4 Me(BuO)P(S)Cl 
• 681-06-1 dimethyl methylphosphonothionate 
• 2524-16-5 O-ethyl methylchlorothiophosphonate 
• 25371-75-9 methyl-thiophosphonic acid O,O'-dipropyl ester 
• 18628-73-4 methylthiophosphoric di-n-butyl ester 
• 34694-00-3 C₁₁H₁₃N₂O₂PS 
• 92162-74-8 N,N'-Dicyclohexyl-methylthiophosphonsaeure-diamid 
• 13953-84-9 2,4-Dimethyl-1,3-bis-tolyl-2,4-dithio-cyclodiphosphazan 
• 13789-66-7 1,3-Bis-(4-chlor-phenyl)-2,4-dimethyl-2,4-dithio-cyclodiphosphazan 
• 18789-43-0 2-methyl-1,3,2-dithiaphospholane, 2-sulfide 
• 21904-86-9 Methyldithiophosphonsaeure-phenylester-butylamid 
• 34694-20-7 C₁₃H₂₀NOPS₂ 
• 22740-38-1 S-Phenylmethylchloriddithiophosphonat 

Relevant academic research and scientific papers

Mass spectral characterization of the CWC-related isomeric dialkyl alkylphosphonothiolates/alkylphosphonothionates under gas chromatography/mass spectrometry conditions

RATIONALE The isomeric dialkyl alkylphosphonothiolates and dialkyl alkylphosphonothionates are listed as scheduled chemicals of the Chemical Weapons Convention (CWC) implemented by the OPCW. The P-S and P-R bond connectivity has to be correctly identified for the verification of the CWC. The present study demonstrates successful identification of the target isomers by selective fragmentation under electron ionization (EI) or chemical ionization (CI) conditions. METHODS All the studied isomeric compounds (27 in total) were synthesized in our laboratory using established methods, then analyzed by EI and CI gas chromatography/mass spectrometry (GC/MS) using an Agilent 6890 gas chromatograph equipped with a HP-5MS capillary column and interfaced to a 5973 N mass-selective detector. The retention index (RI) values of all the compounds were calculated using Van den Dool's formula. GC/MS/MS and GC/HRMS experiments were also performed using a VG-Autospec (magnetic sector) and JEOL-AccuToF (time-of-flight) mass spectrometer, respectively. RESULTS The EI mass spectra of all the compounds had an abundant molecular ion at m/z 182, except in the case of a few selected butyl-substituted compounds, where this ion was of low abundance. The EI fragmentation pathways include α-cleavage, McLafferty rearrangement, McLafferty + 1 rearrangement, O/S-alkyl radical loss, and an alkene loss with a hydrogen shift. The characteristic fragment ions and their relative abundances are significant in elucidating the alkyl group attached to the P/S/O-atoms as well as the P-S/P = S bond connectivity. The EI and CI mass spectra together with RI values enable unambiguous identification of all the studied isomeric compounds. CONCLUSIONS The present study highlights the structural characterization of the isomeric phosphonothiolates and phosphonothionates based on their selective EI fragmentation. The assigned fragmentation pathway helps in the assignment of P-S and P-alkyl connectivity in phosphonothiolates and phosphonothionates, consequently the structure of the unknown compounds. The EI mass spectra (27 compounds) of isomeric compounds are immensely useful in the OPCW official proficiency tests and for off-site analysis. Copyright 2013 John Wiley & Sons, Ltd. Copyright

Microsynthesis and electron ionization mass spectral studies of O(S)-alkyl N,N-dimethyl alkylphosphono(thiolo)thionoamidates for Chemical Weapons Convention verification

RATIONALE The availability of mass spectra and interpretation skills are essential for unambiguous identification of the Chemical Weapons Convention (CWC)-related chemicals. The O(S)-alkyl N,N-dimethyl alkylphosphono(thiolo) thionoamidates are included in the list of scheduled CWC-related compounds, but there are very few spectra from these compounds in the literature. This paper examines these spectra and their mass spectral fragmentation routes. METHODS The title chemicals were prepared through microsynthetic protocols and were analyzed using electron ionization mass spectrometry with gas chromatography as a MS-inlet system. Structures of fragments were confirmed using analysis of fragment ions of deuterated analogs, tandem mass spectrometry and density functional theory (DFT) calculations. RESULTS Mass spectrometric studies revealed some interesting fragmentation pathways during the ionization process, such as alkene and amine elimination and McLafferty-type rearrangements. The most important fragmentation route of the chemicals is the thiono-thiolo rearrangement. DFT calculations are used to support MS results and to reveal relative preference formation of fragment ions. The retention indices (RIs) of all the studied compounds are also reported. CONCLUSIONS Mass spectra of the synthesized compounds were investigated with the aim to enrich the Organization for the Prohibition of Chemical Weapons (OPCW) Central Analytical Database (OCAD) which may be used for detection and identification of CWC-related chemicals during on-site inspection and/or off-site analysis such as OPCW proficiency tests. Copyright

Studies on chiral thiophosphoric acids and their derivatives 16. - The asymmetric cyclization of L-(+)-prolinol with (thio)phosphoro(-no)dichloridates

The cyclizations of L-(+)-prolinol 5 with (thio)phosphoro(-no)dichloridates 6 give 1,2,3-azaphosphaoxabicyclo[3.3.0]octanes 7 consisting of unequal amounts of diastereoisomers, eight pairs of which have been successfully resolved by silica gel column chromatography or recrystallization. The influences of reaction temperature, solvent and substrate concentration upon the asymmetric induction have also been investigated.

DIE STRUKTUR VON ALKYL- UND ARYLPERTHIOPHOSPHONSAEUREANHYDRIDEN IN LOESUNG

The analysis of 1H-, 31P- and 13C-NMR spectra of different alkyl- and arylperthiophosphonic acid anhydrides shows that these compounds prefer a dimeric structure in solution.They exist as 2,4-diorganyl-2,4-dithioxo-1,3,2λ5,4λ5-dithiadiphosphetanes.Most of the perthiophosphonic acid anhydrides form configuration isomers which differ in the position of the thioxo groups relatively to the ring plane.The concentration of the trans-isomer is generally larger than that of the cis-isomer.The ratio of the concentration of both isomers is obviously determined by the polarity of the solvent used.Mixing of solutions of different perthiophosphonic acid anhydrides results in unsymmetrical compounds also existing in cis- and trans-configuration. 31P chemical shifts and geminal P-P coupling constants for symmetrical and unsymmetrical perthiophosphonic acid anhydrides are presented and discussed. - Key words: 31P chemical shifts; P-P coupling constants; perthiophosphonic acid anhydrides; mixed perthiophosphonic acid anhydrides; configuration isomers; 2,4-diorganyl-2,4-dithioxo-1,3,2λ5,4λ5-dithiadiphosphetanes.

SYNTHESIS, REACTIONS, AND STEREOCHEMICAL CORRELATIONS OF AN OPTICALLY ACTIVE TERVALENT PHOSPHORUS THIO ESTER

The tetracovalent (R)-(-)-isopropyl methylphosphionate (2) reacts with methyl trifluoromethanesulfonate to form a phosphonium salt (3), which yields the tervalent (R)-(-)-O-isopropyl S-methyl methylphosphonothioite (4) on treatment with triethylamine.However, the reaction is much less sterespecific (ca. 35percent) than that of the corresponding P=O analog, 1 (ca. 100percent).The (-)-4 product was characterized and its configuration confirmed by conversion into its corresponding P=O and P=S derivatives, (S)-(-)-5 and (R)-(-)-8, respectively, which have been related to the known (S)-(-) and (R)-(+)- O-isopropyl methylphosphnothioic acids (6).The triflate product has also been prepared by a relatively simple asymmetric induction reaction that had been reported for a similar compound, and the stereospecificities of the two procedures are compared.

Process for making compounds possessing anticholinesterase activity

The compounds of S-(2-dialkylaminoalkyl) alkyl phosphonothioic acids and hod of preparing said compounds possessing anticholinesterase activity comprising an aqueous solution which comprises dialkylaminoalkyl chloride salts which are converted to their corresponding dialkylmonoalkyl ammonium ions and alkylphosphonothioic acids forming a reaction mixture. The latter mixture is placed on a cation exchange resin with subsequent addition of water as an eluting agent giving rise to fractions containing the desired compounds.

Process for preparing alkyl or aryl phosphorus halides and mixed isomers thereof

Alkyl or aryl phosphonic or phosphonothioic dihalides and phosphinic or phosphinothioic monohalides are prepared by reacting an alkyl halide or aryl halide respectively with a tri-valent phosphorus compound having at least two halogens attached thereto, and preferably three two halogens such as phosphorus trihalide, in the presence of P4 O10 or P4 S10 under at least autogenous pressure at a temperature of from 200° C. to 450° C. The compounds obtained are useful as constituents in insecticides, fungicides, pharmaceuticals, and as intermediates in preparation of other organophosphorus compounds.

Process for preparing alkyl- or arylphosphonothioic dihalides

Alkyl- or arylphosphonothioic dihalides are prepared by contacting a dialkyl or diaryl thioether with various phosphorus containing reactants including: PCl3, PBr3, P(S)Cl3, P(S)Br3, P4 S3, P4 S5, P4 S7, P4 S1 O and elemental phosphorus under at least autogenous pressure at a temperature of from about 200° C. to about 400° C. The compounds obtained are useful as constituents in insecticides, fungicides, pharmaceuticals, and as intermediates in preparation of other organophosphorus compounds.