Diethyl dithiophosphoric acid

Diethyl dithiophosphoric acid, sometimes mistakenly called diethyl dithiophosphate, is the organophosphorus compound with the formula (C2H5O)2PS2H. It is the processor for production of the organophosphate insecticide Terbufos. Although samples can appear dark, it is a colorless liquid.

Diethyl dithiophosphoric acid
Names
Preferred IUPAC name
O,O-Diethyl hydrogen phosphorodithioate
Other names
O,O-Diethyl dithiophosphoric acid; Diethyl dithiophosphate; Diethyl phosphorodithioate; Diethyl ester of phosphorodithioic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.506
EC Number
  • 206-055-9
PubChem CID
RTECS number
  • TD7350000
UNII
  • InChI=1S/C4H11O2PS2/c1-3-5-7(8,9)6-4-2/h3-4H2,1-2H3,(H,8,9)
    Key: IRDLUHRVLVEUHA-UHFFFAOYSA-N
  • InChI=1/C4H11O2PS2/c1-3-5-7(8,9)6-4-2/h3-4H2,1-2H3,(H,8,9)
    Key: IRDLUHRVLVEUHA-UHFFFAOYAW
SMILES
  • CCOP(=S)(OCC)S
Properties
C4H11O2PS2
Molar mass 186.22 g·mol−1
Appearance colorless liquid
Melting point < 0 °C (32 °F; 273 K)
Boiling point 66 °C (151 °F; 339 K) at 1 mmHg
Hazards
GHS labelling:
Danger
H301, H311, H314, H330
P260, P264, P270, P271, P280, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P361, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
3
2
1
Flash point 82 °C (180 °F; 355 K)
538 °C (1,000 °F; 811 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 500 mg/kg (rabbit, dermal)
4510 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is prepared by treating phosphorus pentasulfide with ethanol:

P2S5 + 4 C2H5OH → 2 (C2H5O)2PS2H + H2S
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