756-80-9

Basic information

• Product Name: Dimethylphosphorodithioate
• Synonyms: dimethyldithio;dimethyldithiophosphate;dimethylphosphodithionate;kwasdwumetylo-dwutiofosforowy;kyselinao,o-dimethyldithiofosforcna;METHOTHIOACID;AURORA KA-1662;DMPTA
• CAS NO: 756-80-9
• Molecular Formula: C₂H₇O₂PS₂
• Molecular Weight: 158.18
• EINECS: 212-053-9
• Mol File: 756-80-9.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 65℃
• Flash Point: 71.2oC
• Appearance: /
• Density: 1.29
• Vapor Pressure: 0.627mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: -20°C
• PKA: -0.10±0.30(Predicted)
• Water Solubility: 226g/L at 20℃
• CAS DataBase Reference: Dimethylphosphorodithioate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethylphosphorodithioate(756-80-9)
• EPA Substance Registry System: Dimethylphosphorodithioate(756-80-9)

Safety Data

• Hazardous Substances Data: 756-80-9(Hazardous Substances Data)

Usage

Chemical Properties

Dimethylphosphorodithioate is a colorless liquid, industrial product is black liquid with a foul odor.

Uses

O,O'-Dimethyl Dithiophosphate can be used as a pesticide intermediate, mainly for the preparation of organophosphorus pesticides such as dimethoate and malathion.

Flammability and Explosibility

Flammable

InChI:InChI=1/C2H7O2PS2/c1-3-5(6,7)4-2/h1-2H3,(H,6,7)/p-1

Synthetic route

methanol (67-56-1) → O,O-dimethyl phosphorodithioic acid (756-80-9)

Conditions	Yield
With pyridine; dmap; tetraphosphorus decasulfide; dimethylsulfide at 25 - 55℃; under 40 Torr; for 1h; Pressure; Temperature; Large scale;	97%
With tetraphosphorus decasulfide In chloroform for 10h; Heating;	88%
With tetraphosphorus decasulfide In toluene at 40℃; for 11.5h; Reflux; Inert atmosphere;	86%

ammonium O,O-dimethyl dithiophosphate → O,O-dimethyl phosphorodithioic acid (756-80-9)

Conditions	Yield
	96.8%

dimethyl S-methyl phosphorodithioate (2953-29-9) + isopropyl alcohol (67-63-0) → dimethyl thiophosphite (5930-72-3) + thiophosphoric acid O-isopropyl ester O',O''-dimethyl ester (75511-31-8) + thiophosphoric acid O-isopropyl ester O',S-dimethyl ester (75511-33-0) + O,O-dimethyl phosphorodithioic acid (756-80-9)

Conditions	Yield
In acetonitrile Product distribution; Mechanism; Quantum yield; Irradiation; var. of solvent, conc., competition with MeOH, further with triplet sensitizers;	A n/a B 66% C 19% D n/a

dimethyl S-methyl phosphorodithioate (2953-29-9) → O,O-dimethyl phosphorodithioic acid (756-80-9)

[(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester (121-75-5) + water (7732-18-5) + acetone (67-64-1) → diethylmalate (7554-12-3) + O,O-dimethyl phosphorodithioic acid (756-80-9)

Conditions	Yield
at 0 - 30℃; Rate constant; pH 9 bis pH 11.Hydrolysis;

methyl iodide (74-88-4) → O,O-dimethyl phosphorodithioic acid (756-80-9)

Conditions	Yield
With sodium hydroxide; dithioorthophosphoric acid; tetraethylammonium iodide In dichloromethane at 20℃; for 0.5h;

S-2-ethylthioethyl O,O-dimethyl phosphorodithioate (640-15-3) + thiophenolate (13133-62-5) → (2-ethylsulfanyl-ethylsulfanyl)-benzene + dithiophosphoric acid S-(2-ethylsulfanyl-ethyl) ester O-methyl ester + methyl-phenyl-thioether (100-68-5) + O,O-dimethyl phosphorodithioic acid (756-80-9)

Conditions	Yield
With tetraborate buffer; sodium chloride In methanol at 25℃; pH=9.20; Kinetics; Further Variations:; Temperatures;

S-2-ethylthioethyl O,O-dimethyl phosphorodithioate (640-15-3) → dimethylthiophosphoric acid (1112-38-5) + 2-(ethylsulfanyl)ethanol (110-77-0) + 2-ethylsulfanyl-ethanethiol (26750-44-7) + O,O-dimethyl phosphorodithioic acid (756-80-9)

Conditions	Yield
With tetraborate buffer; sodium chloride In methanol at 25℃; pH=9.20; Kinetics; Further Variations:; Temperatures; Reagents;

methanol (67-56-1) + tetraphosphorus decasulfide (15857-57-5) → O,O-dimethyl phosphorodithioic acid (756-80-9)

Conditions	Yield
In methanol react. of methanol with P4S10;;

O,O'-Dimethyldithiophosphoric acid ammonium salt (1066-97-3) → O,O-dimethyl phosphorodithioic acid (756-80-9)

Conditions	Yield
With sulfuric acid In dichloromethane at -25 - 25℃; pH=< 2.0;

[(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester (121-75-5) → O,O-dimethyl phosphorodithioic acid (756-80-9)

Conditions	Yield
With 1-butyl-3-methylimidazolium alanine acid salt In acetonitrile at 25℃; Kinetics; Microwave irradiation; Green chemistry;

mesoxalodinitrile 2-chlorophenylhydrazone (55653-03-7) + O,O-dimethyl phosphorodithioic acid (756-80-9) → {[(2-chloro-phenyl)-hydrazono]-cyano-thioacetyl}-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	99%

2-[(2-nitrophenyl)hydrazono]malononitrile (55653-13-9) + O,O-dimethyl phosphorodithioic acid (756-80-9) → {cyano-[(2-nitro-phenyl)-hydrazono]-thioacetyl}-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	99%

2-[(2,5-Dichloro-phenyl)-hydrazono]-malononitrile (1208-17-9) + O,O-dimethyl phosphorodithioic acid (756-80-9) → {cyano-[(2,5-dichloro-phenyl)-hydrazono]-thioacetyl}-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	99%

4-nitrophenylhydrazonopropanedinitrile (3722-12-1) + O,O-dimethyl phosphorodithioic acid (756-80-9) → {cyano-[(4-nitro-phenyl)-hydrazono]-thioacetyl}-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	99%

O,O-dimethyl phosphorodithioic acid (756-80-9) + 2-phenylhydrazonomalononitrile (306-18-3) → [cyano-(phenyl-hydrazono)-thioacetyl]-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	99%

O,O-dimethyl phosphorodithioic acid (756-80-9) + 2-[(4-chlorophenyl)hydrazono]malononitrile (946-76-9) → {[(4-chloro-phenyl)-hydrazono]-cyano-thioacetyl}-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	99%

O,O-dimethyl phosphorodithioic acid (756-80-9) + 2-[(2-Methoxy-phenyl)-hydrazono]-malononitrile (1208-10-2) → {cyano-[(2-methoxy-phenyl)-hydrazono]-thioacetyl}-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	99%

triisopropylgallium (54514-59-9) + O,O-dimethyl phosphorodithioic acid (756-80-9) → O,O'-dimethyldithiophosphatodiisopropylgallane

Conditions	Yield
In benzene byproducts: i-propanol; stoich. amt. of org. compd. soln. addn. dropwise to Ga-compd. soln. over5 min, mixt. stirring under light vac. for 12 h, solvent vac. removal,; elem. anal.;	99%

triisopropyl indium (17144-80-8) + O,O-dimethyl phosphorodithioic acid (756-80-9) → O,O'-dimethyldithiophosphatodiisopropylindane

Conditions	Yield
In benzene byproducts: i-propanol; stoich. amt. of org. compd. soln. addn. dropwise to Ga-compd. soln. over5 min, mixt. stirring under light vac. for 12 h, solvent vac. removal,; elem. anal.;	99%

O,O-dimethyl phosphorodithioic acid (756-80-9) + Diethyl maleate (141-05-9) → [(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester (121-75-5)

Conditions	Yield
With hydrogenchloride In water at 10 - 40℃; for 8h; Reagent/catalyst; Green chemistry;	98%
With triethylamine; hydroquinone
With hydroquinone In water at 53℃; for 8h;
at -30 - -25℃; Inert atmosphere;
With triethylamine; hydroquinone

allylisocyanate (1476-23-9) + O,O-dimethyl phosphorodithioic acid (756-80-9) → O,O-dimethyl-S-(N-allylcarbamoyl) dithiophosphate

Conditions	Yield
In tetrachloromethane	98%

dodecane+O,O-dimethyl-dithiophosphoric acid + O,O-dimethyl phosphorodithioic acid (756-80-9) + Diethyl maleate (141-05-9) → [(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester (121-75-5)

Conditions	Yield
With sodium hydrogencarbonate In dodecane	98%

Ti(O-t-Am)4 (10585-26-9) + O,O-dimethyl phosphorodithioic acid (756-80-9) → bis(tert-amyloxy)bis(O,O'-dimethyl dithiophosphato)titanium(IV)

Conditions	Yield
In dichloromethane byproducts: C2H5C(CH3)2OH; room temp., 4 h (pale yellow soln.); solvent pumped off; elem. anal.;	98%

titanium(IV) isopropylate (546-68-9) + O,O-dimethyl phosphorodithioic acid (756-80-9) → diisopropoxybis(O,O'-dimethyl dithiophosphato)titanium(IV)

Conditions	Yield
In dichloromethane byproducts: (CH3)2CHOH; room temp., 4 h (pale yellow soln.); solvent pumped off; elem. anal.;	98%

2-[(3-methoxyphenyl)-hydrazono]malononitrile (1208-93-1) + O,O-dimethyl phosphorodithioic acid (756-80-9) → {cyano-[(3-methoxy-phenyl)-hydrazono]-thioacetyl}-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	97%

diphenylguanidine (102-06-7) + O,O-dimethyl phosphorodithioic acid (756-80-9) → N,N'-Diphenyl-guanidine; compound with dithiophosphoric acid O,O'-dimethyl ester (135672-74-1)

Conditions	Yield
In chloroform for 0.25h; Ambient temperature; other diorganyldithiophosphoric acids;	96%
In chloroform for 0.25h; Ambient temperature;	96%

carbonyl cyanide m-chlorophenylhydrazone (555-60-2) + O,O-dimethyl phosphorodithioic acid (756-80-9) → {[(3-chloro-phenyl)-hydrazono]-cyano-thioacetyl}-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	96%

Propargylic aldehyde (624-67-9) + O,O-dimethyl phosphorodithioic acid (756-80-9) → 3-(dimethoxyphosphinothioylthio)acrolein (95601-21-1)

Conditions	Yield
In tetrachloromethane at 25℃; for 16h;	95%

N-(2,2,2-trichloroethylidene)acetamide (26404-44-4) + O,O-dimethyl phosphorodithioic acid (756-80-9) → O,O-dimethyl S-(1-acetamido-2,2,2-trichloroethyl) phosphorodithioate (75320-60-4)

Conditions	Yield
In benzene	95%

hexamethyldisilathiane (3385-94-2) + O,O-dimethyl phosphorodithioic acid (756-80-9) → O,O-dimethyl dithiophosphoric acid S-trimethylsilyl ester (18135-34-7)

Conditions	Yield
at 50℃; for 0.5h;	95%

O,O-dimethyl phosphorodithioic acid (756-80-9) → dimethyl chlorothiophosphate (2524-03-0)

Conditions	Yield
With chlorine; iron In water at 50℃; for 6h;	94.3%
With chlorine at 30 - 40℃; for 3h; Temperature; Green chemistry;	92.1%
With chlorine; benzene
With chlorine In tetrachloromethane at 0℃; Inert atmosphere;
With chlorine; benzene

O,O-dimethyl phosphorodithioic acid (756-80-9) + tin(ll) chloride → C2H7Cl2O3PSSn

Conditions	Yield
In ethanol at 5℃; Inert atmosphere;	93.5%

tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate (53317-87-6) + O,O-dimethyl phosphorodithioic acid (756-80-9) → (CH3O)2P(SAuP(C6H5)3)2(1+)*BF4(1-) = [(CH3O)2P(SAuP(C6H5)3)2](BF4)

Conditions	Yield
With NaBF4 In dichloromethane (N2); excess (EtO)2P(S)SH; stirring (1 h); crystn. (CHCl3, layering with Et2O); elem. anal.;	92%

O,O-dimethyl phosphorodithioic acid (756-80-9) + 2-[2-(2-methylphenyl)hydrazono]malononitrile (55653-08-2) → [cyano-(o-tolyl-hydrazono)-thioacetyl]-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	91%

diallyl(dimethyl)silane (1113-12-8) + O,O-dimethyl phosphorodithioic acid (756-80-9) → me2Si{pr-2-SPS(Ome)2}2

Conditions	Yield
In not given addn. of HSPS(OCH3)2 to a 5-10% excess of (CH3)2Si(CH2CHCH2)2;;	90%

tetramethyl ammoniumhydroxide (75-59-2) + O,O-dimethyl phosphorodithioic acid (756-80-9) → {N(CH3)4}(1+)*{CH3OPOCH3S2}(1-)={N(CH3)4}{CH3OPOCH3S2}

Conditions	Yield
In water; toluene	90%

O,O-dimethyl phosphorodithioic acid (756-80-9) + 2-[2-(3-methylphenyl)hydrazono]malononitrile (3722-14-3) → [cyano-(m-tolyl-hydrazono)-thioacetyl]-thiophosphoramidic acid O,O'-dimethyl ester

Conditions	Yield
With sodium ethanolate In benzene at 20℃; Addition;	90%

Upstream product

• 2953-29-9 dimethyl S-methyl phosphorodithioate 
• 67-63-0 isopropyl alcohol 
• 121-75-5 [(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester 
• 1066-97-3 O,O'-Dimethyldithiophosphoric acid ammonium salt 
• 67-56-1 methanol 
• 15857-57-5 tetraphosphorus decasulfide 
• 640-15-3 S-2-ethylthioethyl O,O-dimethyl phosphorodithioate 
• 13133-62-5 thiophenolate 
• 74-88-4 methyl iodide 
• 7732-18-5 water 
• 67-64-1 acetone 

Downstream Products

• 2253-43-2 O_.O-Dipropyl-dithyophosphat 
• 121-75-5 [(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester 
• 109440-07-5 disulfidothiophosphoric acid O,O'-dimethyl ester-S-S-(4-nitro-phenyl ester) 
• 3700-91-2 dimethoxythiophosphorylsulfanyl-succinic acid dipropyl ester 
• 3700-90-1 dimethoxythiophosphorylsulfanyl-succinic acid diisopropyl ester 
• 5114-31-8 dithiophosphoric acid S-(4-chloro-phenyl ester)-O,O'-dimethyl ester 
• 117880-74-7 disulfidothiophosphoric acid S-S-(4-chloro-2-nitro-phenyl ester)-O,O'-dimethyl ester 
• 18547-52-9 bis-(2-dimethoxythiophosphorylsulfanyl-propyl)-methyl-phenyl-silane 
• 2524-03-0 dimethyl chlorothiophosphate 
• 10541-97-6 Dithiophosphorsaeure-S-(2-hydroxy-1-phenyl-ethyl)-O,O'-dimethylester 
• 2669-32-1 lythidathion 
• 1066-97-3 O,O'-Dimethyldithiophosphoric acid ammonium salt 
• 950-37-8 methidathion 
• 35348-97-1 dithiophosphoric acid O,O'-dimethyl ester S-[2-methylsulfanyl-1-(2-oxo-5-phenyl-[1,3,4]oxadiazol-3-yl)-ethyl] ester 

Relevant articles and documents

Kinetic Study of the Homogenous Methanolysis of Tetraphosphorus Decasulphide

The rate of homogenous methanolysis of pure P4S10, dissolved is CS2, has been measured at 0, 15, 25, and 35 deg C for various MeOH:P4S10 molar ratios.The sole product detected was (MeO)2PS2H.At not too low concentrations, the reaction is virtually first order in and second order in , owing probably to an autocatalytic process.The multistep reaction is kinetically controlled by the initial attack on P4S10; this is tentatively explainedby the rigidity and geometry of the P4S10 molecule and/or by the spontaneous formation of reactive dithioxophosphoranes ZP(=S)2 P(S)S-> from all alcoholysis intermediates.Calculaed activation parameters are discussed.Novel data on the solubility of P4S10 are reported.

Malathion hapten, artificial antigen and preparation method thereof (by machine translation)

The synthetic steps of the invention, are simple and convenient, raw materials are easily available (I), the reaction conditions are mild, and the preparation method of the malathion hapten n＝1-9. can be applied to a rapid detection method for establishment of malathion and a detection requirement, for developing the malathion residues; of the malathion artificial antigen, are shown, through, of the present invention can induce the production, of malathion phosphorus as a starting material, and the preparation method of the human immunogen immunized animal, can be applied to laboratory and factory production . The invention, discloses a method, for rapidly detecting malathion and a, preparation method of the artificial antigen. (by machine translation)

Synthesizing method of O,O-dimethyl phosphorodithioate

The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesizing method of O,O-dimethyl phosphorodithioate. The synthesizing method of the O,O-dimethyl phosphorodithioate has the advantages that on the basis of existing technical method, a proper catalyst is further screened, added into a methanol solution and dripped into a sulfide mother liquid, so that the content and yield of the target product are further increased; the whole methanol dripping process is performed under the micro-negative pressure condition, so that the step of dripping the methanol to react can be performed at lower temperature of 25 to 35 DEG C, and the reaction product of hydrogen sulfide can escape out at micro-negative pressure of 30 to 50mmHg, so as to effectively accelerate the reaction to perform along the positive direction.

Dialkyl (alkylene) dithiophosphate adducts of anhydrous stannous chloride: Synthesis, characterization, and biological activities

Dialkyl (alkylene) dithiophosphate adducts of stannous chloride were synthesized by the reaction of anhydrous tin(II) chloride (SnCl2) and dialkyl (alkylene) dithiophosphoric acid in a 1:1 molar ratio, under anhydrous reaction conditions, below 5 °C in a closed vessel. The newly synthesized adducts were characterized by physicochemical and spectroscopic techniques [FT-IR, NMR (1H, 31P, and 119Sn), and mass spectrometry]. Coordination modalities have indicated a donor-acceptor interaction between sulfur and tin(II) moieties, where tin(II) acts as a Lewis acid. The adducts were found to have significant antibacterial activity against Escherichia coli and Pseudomonas aeruginosa, and antifungal activity against Aspergillus niger and Candida albicans. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.