Thionyl chloride

Thionyl chloride
Names
	IUPAC name Thionyl chloride
	Other names Thionyl dichloride; Sulfurous oxychloride; Sulfinyl chloride; Sulfinyl dichloride; Dichlorosulfoxide; Sulfur oxide dichloride; Sulfur monoxide dichloride; Sulfuryl(IV) chloride;
Identifiers
CAS Number	7719-09-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29290 ;
ChemSpider	22797 ;
ECHA InfoCard	100.028.863
EC Number	231-748-8;
PubChem CID	24386;
RTECS number	XM5150000;
UNII	4A8YJA13N4 ;
UN number	1836
CompTox Dashboard (EPA)	DTXSID3064778 ;
	InChI InChI=1S/Cl2OS/c1-4(2)3 Key: FYSNRJHAOHDILO-UHFFFAOYSA-N ; InChI=1/Cl2OS/c1-4(2)3 Key: FYSNRJHAOHDILO-UHFFFAOYAN;
	SMILES ClS(Cl)=O;
Properties
Chemical formula	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)
Solubility in water	Reacts
Solubility	Soluble in most aprotic solvents: toluene, chloroform, diethyl ether. Reacts with protic solvents such as alcohols
Vapor pressure	384 Pa (−40 °C); 4.7 kPa (0 °C); 15.7 kPa (25 °C);
Refractive index (nD)	1.517 (20 °C)
Viscosity	0.6 cP
Structure
Molecular shape	pyramidal
Dipole moment	1.44 D
Thermochemistry
Heat capacity (C)	121.0 J/mol (liquid)
Std molar; entropy (S⦵298)	309.8 kJ/mol (gas)
Std enthalpy of; formation (ΔfH⦵298)	−245.6 kJ/mol (liquid)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Very toxic, corrosive, releases HCl on contact with water
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H314, H331
Precautionary statements	P261, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	4 0 2 W
Flash point	Non-flammable
	NIOSH (US health exposure limits):
PEL (Permissible)	None
REL (Recommended)	C 1 ppm (5 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related Thionyl halides	Thionyl fluoride; Thionyl bromide; Thionyl iodide;
Related compounds	Sulfuryl chloride; Selenium oxydichloride;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

[1] 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)

[2] Patnaik, Pradyot (2003). Handbook of Inorganic Chemicals. New York, NY: McGraw-Hill. ISBN 0-07-049439-8.

[CRC-3] 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.

[PGCH-4] NIOSH Pocket Guide to Chemical Hazards. "#0611". National Institute for Occupational Safety and Health (NIOSH).

[5] 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.

[6] 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.

[7] 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.

[8] 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.

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Names



IUPAC name Thionyl chloride
Other names Thionyl dichloride Sulfurous oxychloride Sulfinyl chloride Sulfinyl dichloride Dichlorosulfoxide Sulfur oxide dichloride Sulfur monoxide dichloride Sulfuryl(IV) chloride
Identifiers
CAS Number	7719-09-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29290^Y
ChemSpider	22797^Y
ECHA InfoCard	100.028.863
EC Number	231-748-8
PubChem CID	24386
RTECS number	XM5150000
UNII	4A8YJA13N4^N
UN number	1836
CompTox Dashboard (EPA)	DTXSID3064778
InChI InChI=1S/Cl2OS/c1-4(2)3^Y Key: FYSNRJHAOHDILO-UHFFFAOYSA-N^Y InChI=1/Cl2OS/c1-4(2)3 Key: FYSNRJHAOHDILO-UHFFFAOYAN
SMILES ClS(Cl)=O
Properties
Chemical formula	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)
Solubility in water	Reacts
Solubility	Soluble in most aprotic solvents: toluene, chloroform, diethyl ether. Reacts with protic solvents such as alcohols
Vapor pressure	384 Pa (−40 °C) 4.7 kPa (0 °C) 15.7 kPa (25 °C)^[1]
Refractive index (n_D)	1.517 (20 °C)^[2]
Viscosity	0.6 cP
Structure
Molecular shape	pyramidal
Dipole moment	1.44 D
Thermochemistry
Heat capacity (C)	121.0 J/mol (liquid)^[3]
Std molar entropy (S^⦵₂₉₈)	309.8 kJ/mol (gas)^[3]
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	−245.6 kJ/mol (liquid)^[3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Very toxic, corrosive, releases HCl on contact with water
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H314, H331
Precautionary statements	P261, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	4 0 2 W
Flash point	Non-flammable
NIOSH (US health exposure limits):
PEL (Permissible)	None^[4]
REL (Recommended)	C 1 ppm (5 mg/m³)^[4]
IDLH (Immediate danger)	N.D.^[4]
Related compounds
Related Thionyl halides	Thionyl fluoride Thionyl bromide Thionyl iodide
Related compounds	Sulfuryl chloride Selenium oxydichloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references