Back كلوريد الثيونيل Arabic تیونیل کولورید AZB Clorur de tionil Catalan Chlorid thionylu Czech Thionylchlorid German Tionila klorido Esperanto Cloruro de tionilo Spanish تیونیل کلرید Persian Tionyylikloridi Finnish Chlorure de thionyle French
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| Names | |
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| IUPAC name
Thionyl chloride
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.028.863 |
| EC Number |
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PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 1836 |
CompTox Dashboard (EPA)
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| Properties | |
| SOCl2 | |
| Molar mass | 118.97 g/mol |
| Appearance | Colourless liquid (yellows on ageing) |
| Odor | Pungent and unpleasant |
| Density | 1.638 g/cm3, liquid |
| Melting point | −104.5 °C (−156.1 °F; 168.7 K) |
| Boiling point | 74.6 °C (166.3 °F; 347.8 K) |
| Reacts | |
| Solubility | Soluble in most aprotic solvents: toluene, chloroform, diethyl ether. Reacts with protic solvents such as alcohols |
| Vapor pressure |
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Refractive index (nD)
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1.517 (20 °C)[2] |
| Viscosity | 0.6 cP |
| Structure | |
| pyramidal | |
| 1.44 D | |
| Thermochemistry | |
Heat capacity (C)
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121.0 J/mol (liquid)[3] |
Std molar
entropy (S⦵298) |
309.8 kJ/mol (gas)[3] |
Std enthalpy of
formation (ΔfH⦵298) |
−245.6 kJ/mol (liquid)[3] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Very toxic, corrosive, releases HCl on contact with water |
| GHS labelling: | |
  
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| Danger | |
| H302, H314, H331 | |
| P261, P280, P305+P351+P338, P310 | |
| NFPA 704 (fire diamond) | |
| Flash point | Non-flammable |
| NIOSH (US health exposure limits): | |
PEL (Permissible)
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None[4] |
REL (Recommended)
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C 1 ppm (5 mg/m3)[4] |
IDLH (Immediate danger)
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N.D.[4] |
| Related compounds | |
Related Thionyl halides
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thionyl chloride is an inorganic compound with the chemical formula SOCl2. It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes (50,000 short tons) per year being produced during the early 1990s,[5] but is occasionally also used as a solvent.[6][7][8] It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.
Thionyl chloride is sometimes confused with sulfuryl chloride, SO2Cl2, but the properties of these compounds differ significantly. Sulfuryl chloride is a source of chlorine whereas thionyl chloride is a source of chloride ions.
- ^ Thionyl chloride in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-11)
- ^ Patnaik, Pradyot (2003). Handbook of Inorganic Chemicals. New York, NY: McGraw-Hill. ISBN 0-07-049439-8.
- ^ a b c Lide, David R.; et al., eds. (1996). CRC Handbook of Chemistry and Physics (76th ed.). Boca Raton, FL: CRC Press. pp. 5–10. ISBN 0-8493-0476-8.
- ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0611". National Institute for Occupational Safety and Health (NIOSH).
- ^ Lauss, H.-D.; Steffens, W. "Sulfur Halides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a25_623. ISBN 978-3527306732.
- ^ Oka, Kitaro (1981). "Some Applications of Thionyl Chloride in Synthetic Organic Chemistry". Synthesis. 1981 (9): 661–681. doi:10.1055/s-1981-29563. S2CID 94917739.
- ^ Calderazzo, Fausto; Dell'Amico, Daniela Belli (April 1981). "Syntheses of carbonyl halides of late transition elements in thionyl chloride as solvent. Carbonyl complexes of palladium(II)". Inorganic Chemistry. 20 (4): 1310–1312. doi:10.1021/ic50218a072.
- ^ Garber, E. B.; Pease, L. E. D.; Luder, W. F. (20 April 1953). "Titration of Aprotic Acids in Thionyl Chloride". Analytical Chemistry. 25 (4): 581–583. doi:10.1021/ac60076a012.