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| Names | |||
|---|---|---|---|
| IUPAC name Phosphorothioic trichloride | |||
| Other names Thiophosphoryl chloride | |||
| Identifiers | |||
| CAS Number | |||
| 3D model (JSmol) | |||
| ChemSpider | |||
| ECHA InfoCard | 100.021.476 
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| PubChem CID | |||
| CompTox Dashboard (EPA) | |||
InChI
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SMILES
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| Properties | |||
| Chemical formula | Cl3PS | ||
| Molar mass | 169.4 g/mol | ||
| Appearance | Colorless liquid | ||
| Density | 1.67 g/cm | ||
| Melting point | −35 °C (987 K) | ||
| Boiling point | 125 °C (1685 K) | ||
| Solubility in water | Reacts | ||
| Solubility | Soluble in benzene, Chloroform, CS2 and CCl4. | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
| Main hazards | Violent hydrolysis | ||
| Flash point | ?°C | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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Thiophosphoryl chloride is an inorganic compound with the formula PSCl3. Thiophosphoryl chloride, PSCl3, is a fuming, colorless liquid with a pungent odor. It is synthesized from phosphorus chloride and used to thiophosphorylate organic compounds, such as to produce insecticides.
Synthesis
Thiophosporyl chloride can be generated by several reactions starting from phosphorus trichloride. The most common and practical synthesis, hence used in industrial manufacturing, is directly reacting phosphorus trichloride with excess sulfur at 180 °C.
- PCl3 + S → PSCl3
Using this method, yields can be very high after purification by distillation. Catalysts can further the reaction at lower temperatures, but are not necessary. Alternatively, the reaction of phosphorus pentasulfide and phosphorus pentachloride also affords thiophosporyl chloride in yields around 70%.
- 3 PCl5 + P2S5 → 5 PSCl3
Reactions
PSCl3 is soluble in benzene, carbon tetrachloride, chloroform, and carbon disulfide. However, it hydrolyzes rapidly in basic or hydroxylic solutions, such as alcohols and amines, to produce thiophosphates.
- PSCl3 + 4 H2O → H3PO4 + H2S + 3 HCl
- PSCl3 + H2O → HOP(S)Cl2 + HCl
PSCl3 is used to thiophosphorylate, or add P=S, organic compounds. This conversion is widely applicable for amines and alcohols, as well as amino alcohols, diols, and diamines. Industrially, PSCl3 is primarily used to produce insecticides, like parathion.
- PSCl3 + 2 C2H5OH → (C2H5O)2PSCl + 2 HCl
- (C2H5O)2PSCl + NaOC6H4NO2 → (C2H5O)2PSOC6H4NO2 + NaCl
PSCl3 reacts with tertiary amides to generate thioamides. For example:
- C6H5C(O)N(CH3)2 + PSCl3 → C6H5C(S)N(CH3)2 + POCl3
References
- ^ Spilling, C. D. "Thiophosphoryl Chloride" in Encyclopedia of Reagents for Organic Synthesis John Wiley & Sons, Weinheim, 2001. doi:10.1002/047084289X.rt104. Article Online Posting Date: April 15, 2001.
- ^ Betterman, G.; Krause, W.; Riess, G.; Hofmann, T. “Phosphorus Compounds, Inorganic” Ullman’s Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York, 2005. doi:10.1002/14356007.a19_527. Cite error: The named reference "betterman" was defined multiple times with different content (see the help page).
- Martin, D. R.; Duvall, W. M. “Phosphorus (V) Sulfochloride” Inorganic Syntheses, Volume IV. McGraw-Hill, 1953. doi:10.1002/9780470132357.ch24.
- Fee, D. C.; Gard, D. R.; Yang, C. “Phosphorus Compounds” Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons: New York, 2005. doi:10.1002/0471238961.16081519060505.a01.pub2.