Thiophosphoryl chloride
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| Thiophosphoryl chloride | |
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| IUPAC name | Thiophosphoryl chloride |
| Identifiers | |
| CAS number | [3982-91-0] |
| Properties | |
| Molecular formula | Cl3PS |
| Molar mass | 169.4 g/mol |
| Appearance | Colorless liquid |
| Density | 1,67 g/cm³ |
| Melting point |
-35 °C (987 K) |
| Boiling point |
125 °C (1685 K) |
| Solubility in water | benzene, CS2 |
| Hazards | |
| MSDS | Magnesium chloride MSDS |
| Main hazards | violent hydrolysis |
| Flash point | ?°C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Thiophosphoryl chloride is an inorganic compound with the formula PSCl3. [1] 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.
[edit] 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 ºC. [2]
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]
3PCl5 + P2S5 → 5PSCl3
[edit] Reactions
PSCl3 is soluble in benzene, carbon tetrachloride, chloroform, and carbon disulfide.[1] However, it hydrolyzes rapidly in basic or hydroxylic solutions, such as alcohols and amines, to produce thiophosphates.[2]
- PSCl3 + 4H2O → H3PO4 + H2S + 3HCl
- PSCl3 + H2O → HOP(S)Cl2 + HCl
PSCl3 is used to thiophosphorylate, or add P=S, organic compounds.[2] This conversion is widely applicable for amines and alcohols, as well as amino alcohols, diols, and diamines.[1] Industrially, PSCl3 is primarily used to produce insecticides, like parathion.[4]
- PSCl3 + 2C2H5OH → (C2H5O)2PSCl + 2HCl
- (C2H5O)2PSCl + NaOC6H4NO2 → (C2H5O)2PSOC6H4NO2 + NaCl
PSCl3 reacts with tertiary amides to generate thioamides.[1] For example:
- C6H5C(O)N(CH3)2 + PSCl3 → C6H5C(S)N(CH3)2 + POCl3
[edit] References
- ^ a b c d 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.
- ^ a b c 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 .
- ^ 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.
