Dichlorodiethyl sulfone

Dichlorodiethyl sulfone
Names
	Preferred IUPAC name 1-Chloro-2-(2-chloroethane-1-sulfonyl)ethane
	Other names Bis(2-chloroethyl) sulfone, mustard sulfone, Yperite sulfone, H sulfone
Identifiers
CAS Number	471-03-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	9705;
PubChem CID	10109;
UNII	DZ4S6T48FY ;
CompTox Dashboard (EPA)	DTXSID50197035 ;
	InChI InChI=1S/C4H8Cl2O2S/c5-1-3-9(7,8)4-2-6/h1-4H2 Key: LUYAMNYBNTVQJG-UHFFFAOYSA-N;
	SMILES C(CCl)S(=O)(=O)CCCl;
Properties
Chemical formula	C4H8Cl2O2S
Molar mass	191.07 g·mol−1
Melting point	52 °C (126 °F; 325 K)
Solubility	ethanol; ether; chloroform
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H312
Precautionary statements	P264, P270, P280, P301+P310, P302+P352, P312, P321, P322, P330, P363, P405, P501
Related compounds
Related compounds	mustard gas, mustard sulfoxide; Dibromodiethyl sulfone
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dichlorodiethyl sulfone (or mustard sulfone) is an oxidation product of mustard gas. It has the formula (ClCH₂CH₂)₂SO₂. Although it is irritating to the eyes, it is not nearly as bad as mustard gas (dichlorodiethyl sulfide).^[1]^[2]

Structure

The all-trans arrangement is predicted by Hartree-Fock computational methods to be the most stable conformer.^[3]

Reactions

When refluxed with aqueous sodium hydroxide, oxygen replaces the chlorine, and an 1,4-oxathiane ring is formed, p-oxathiane-4,4-dioxide.^[4] When treated with sodium carbonate, a weaker base, bis-(hydroxyethyl)sulfone is the major product formed.^[4] In comparison the dehydrochlorination of the sulfoxide is much slower.^[4]

References

^ Lewis, Robert A. (2016). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. p. 452. ISBN 978-1-119-26784-3.
^ Transactions of the Annual Conference of State Sanitary Engineers. 1943. p. 3–175.
^ White, William E.; Sobus, Micah J.; Okerberg, Brian c. (November 1998). "Conformations Of Mustard Sulfoxide And Mustard Sulfone". Phosphorus, Sulfur, and Silicon and the Related Elements. 142 (1): 149–165. doi:10.1080/10426509808029673.
^ ^a ^b ^c Breslow, David S.; Skolnik, Herman (2009). Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles. John Wiley & Sons. p. 836. ISBN 978-0-470-18833-0.

[1] Lewis, Robert A. (2016). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. p. 452. ISBN 978-1-119-26784-3.

[2] Transactions of the Annual Conference of State Sanitary Engineers. 1943. p. 3–175.

[3] White, William E.; Sobus, Micah J.; Okerberg, Brian c. (November 1998). "Conformations Of Mustard Sulfoxide And Mustard Sulfone". Phosphorus, Sulfur, and Silicon and the Related Elements. 142 (1): 149–165. doi:10.1080/10426509808029673.

[multi-4] Breslow, David S.; Skolnik, Herman (2009). Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles. John Wiley & Sons. p. 836. ISBN 978-0-470-18833-0.

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