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Dimethyl dithiophosphoric acid

(Redirected from Diorganodithiophosphate)

Dimethyl dithiophosphoric acid is the organophosphorus compound with the formula (CH3O)2PS2H. It is the processor for production of the organothiophosphate insecticide Malathion. Although samples can appear dark, the compound is a colorless, distillable liquid.[1]

Dimethyl dithiophosphoric acid
Names
Preferred IUPAC name
O,O-Dimethyl phosphorodithioate
Other names
O,O-Dimethyl dithiophosphoric acid; Dimethyl dithiophosphate; Dimethyl phosphorodithioate; Dimethyl ester of phosphorodithioic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.958 Edit this at Wikidata
EC Number
  • 212-053-9
UNII
  • InChI=1S/C2H7O2PS2/c1-3-5(6,7)4-2/h1-2H3,(H,6,7)
    Key: CZGGKXNYNPJFAX-UHFFFAOYSA-N
  • InChI=1/C2H7O2PS2/c1-3-5(6,7)4-2/h1-2H3,(H,6,7)
    Key: CZGGKXNYNPJFAX-UHFFFAOYAT
  • COP(=S)(OC)S
Properties
C2H7O2PS2
Molar mass 158.17 g·mol−1
Appearance colorless liquid
Boiling point 62–64 °C (144–147 °F; 335–337 K) 0.5 mm Hg
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
H226, H242, H290, H302, H314, H332, H361, H412
P201, P202, P210, P233, P234, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P363, P370+P378, P390, P403+P235, P404, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
2
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

It is prepared by treating phosphorus pentasulfide with methanol:[2]

P2S5 + 4 CH3OH → 2 (CH3O)2PS2H + H2S

See also

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References

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  1. ^ J. Svara, N. Weferling, T. Hofmann "Phosphorus Compounds, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a19_545.pub2
  2. ^ Lefferts, J. L.; Molloy, K. C.; Zuckerman, J. J.; Haiduc, I.; Guta, C.; Ruse, D., "Oxy and thio phosphorus acid derivatives of tin. 1. Triorganotin(IV) dithiophosphate esters", Inorganic Chemistry 1980, volume 19, 1662-1670. doi:10.1021/ic50208a046
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