Dichlorodiethyl sulfone

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Dichlorodiethyl sulfone
Dichlorodiethyl sulfone.svg
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
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C4H8Cl2O2S/c5-1-3-9(7,8)4-2-6/h1-4H2
    Key: LUYAMNYBNTVQJG-UHFFFAOYSA-N
  • C(CCl)S(=O)(=O)CCCl
Properties
C4H8Cl2O2S
Molar mass 191.07 g·mol−1
Melting point 52 °C (126 °F; 325 K)
Solubility ethanol; ether; chloroform
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation mark
Danger
H301, H312
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).

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[edit]

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

Reactions[edit]

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[edit]

  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.
  4. ^ 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.