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756-80-9

Basic Information
CAS No.: 756-80-9
Name: Dimethylphosphorodithioate
Article Data: 38
Molecular Structure:
Molecular Structure of 756-80-9 (Dimethylphosphorodithioate)
Formula: C2H7 O2 P S2
Molecular Weight: 158.182
Synonyms: Methylphosphorodithioate (6CI,7CI); O,O-Dimethyl dithiophosphate; O,O-Dimethyldithiophosphoric acid; O,O-Dimethyl hydrogen dithiophosphate; O,O-Dimethylphosphorodithioate; O,O-Dimethyl phosphorodithioic acid; O,O'-Dimethyldithiophosphate; O,O'-Dimethyl hydrogen dithiophosphate
EINECS: 212-053-9
Density: 1.29
Boiling Point: 65℃
Flash Point: 71.2oC
Solubility: 226g/L at 20℃
Safety: Moderately toxic by ingestion. A skin and severe eye irritant. When heated to decomposition it emits very toxic fumes of POx and SOx. See also ESTERS.
PSA: 99.16000
LogP: 2.08410
Synthetic route
67-56-1

methanol

756-80-9

O,O-dimethyl phosphorodithioic acid

Conditions
ConditionsYield
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

756-80-9

O,O-dimethyl phosphorodithioic acid

Conditions
ConditionsYield
96.8%
2953-29-9

dimethyl S-methyl phosphorodithioate

67-63-0

isopropyl alcohol

A

5930-72-3

dimethyl thiophosphite

B

75511-31-8

thiophosphoric acid O-isopropyl ester O',O''-dimethyl ester

C

75511-33-0

thiophosphoric acid O-isopropyl ester O',S-dimethyl ester

D

756-80-9

O,O-dimethyl phosphorodithioic acid

Conditions
ConditionsYield
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
2953-29-9

dimethyl S-methyl phosphorodithioate

756-80-9

O,O-dimethyl phosphorodithioic acid

121-75-5

[(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester

67-64-1

acetone

A

7554-12-3

diethylmalate

B

756-80-9

O,O-dimethyl phosphorodithioic acid

Conditions
ConditionsYield
at 0 - 30℃; Rate constant; pH 9 bis pH 11.Hydrolysis;
74-88-4

methyl iodide

756-80-9

O,O-dimethyl phosphorodithioic acid

Conditions
ConditionsYield
With sodium hydroxide; dithioorthophosphoric acid; tetraethylammonium iodide In dichloromethane at 20℃; for 0.5h;
640-15-3

S-2-ethylthioethyl O,O-dimethyl phosphorodithioate

13133-62-5

thiophenolate

A

(2-ethylsulfanyl-ethylsulfanyl)-benzene

B

dithiophosphoric acid S-(2-ethylsulfanyl-ethyl) ester O-methyl ester

C

100-68-5

methyl-phenyl-thioether

D

756-80-9

O,O-dimethyl phosphorodithioic acid

Conditions
ConditionsYield
With tetraborate buffer; sodium chloride In methanol at 25℃; pH=9.20; Kinetics; Further Variations:; Temperatures;
640-15-3

S-2-ethylthioethyl O,O-dimethyl phosphorodithioate

A

1112-38-5

dimethylthiophosphoric acid

B

110-77-0

2-(ethylsulfanyl)ethanol

C

26750-44-7

2-ethylsulfanyl-ethanethiol

D

756-80-9

O,O-dimethyl phosphorodithioic acid

Conditions
ConditionsYield
With tetraborate buffer; sodium chloride In methanol at 25℃; pH=9.20; Kinetics; Further Variations:; Temperatures; Reagents;
67-56-1

methanol

15857-57-5

tetraphosphorus decasulfide

756-80-9

O,O-dimethyl phosphorodithioic acid

Conditions
ConditionsYield
In methanol react. of methanol with P4S10;;
1066-97-3

O,O'-Dimethyldithiophosphoric acid ammonium salt

756-80-9

O,O-dimethyl phosphorodithioic acid

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

MF: C2H7O2PS2
MW: 158.18
EINECS: 212-053-9
Flash Point: 71.2 °C
Density: 1.29 g/cm3
Refractive index: 1.535
Enthalpy of Vaporization: 41.27 kJ/mol 
Boiling Point: 194.1 °C at 760 mmHg 
IUPAC Name: Dimethoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane
Vapour Pressure of Phosphorodithioic acid , O,O-Dimethyldithiophosphate (756-80-9): 0.627 mmHg at 25°C 
Synonyms: Dimethyldithio ; Dimethyldithiophosphate ; Dimethylphosphodithionate ; Kwasdwumetylo-dwutiofosforowy ; Kyselinao,o-dimethyldithiofosforcna ; Kyselinao,o-dimethyldithiofosforcna(czech) ; Methylphosphorodithioate ; O,O-Dimethyldithiophosphate
Following is the molecular structure of Phosphorodithioic acid , O,O-Dimethyldithiophosphate (756-80-9):

Uses

Phosphorodithioic acid , O,O-Dimethyldithiophosphate (756-80-9) is used as a pesticide intermediate, mainly used for preparation of dimethoate, malathion and other organophosphorus pesticides.

Production

Production methods: Dimethyl sulfide is obtained from the phosphorus pentasulfide with methanol esterification reaction .
Add a certain amount of sulfur and phosphorus pentasulfide according to mass ratio of about 0.7:1  to reaction tank at a certain molar ratio under stirring methanol was added dropwise to control the dropping temperature of 40 ~ 45 ℃, about 2h plus finished, and then at 50 ~ 55 ℃ continue stirring reaction at about 2h, cooled to 35 ℃ out of material that was finished, the yield of 75% or more. The reaction of hydrogen sulfide absorption tower in import absorption with alkali.There are also a new technology of the use of catalytic synthesis of methyl sulfide, improved product quality and yield. Through the appropriate choice of catalyst and some reaction conditions, can be dimethyl sulfide content of an average of 94.20%, the yield of an average of 93.84%.

Toxicity Data With Reference

1.    

skn-rbt 20 mg/24H MOD

    85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,1175.
2.    

eye-rbt 250 µg/24H SEV

    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,211.
3.    

orl-rat LDLo:1000 mg/kg

    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,211.
4.    

orl-mus LD50:1550 mg/kg

    JAFCAU    Journal of Agricultural and Food Chemistry. 28 (1980),599.

Consensus Reports

Phosphorodithioic acid , O,O-Dimethyldithiophosphate (756-80-9) is reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by ingestion. A skin and severe eye irritant. When heated to decomposition it emits very toxic fumes of POx and SOx.