Dichlorodiethyl sulfone
Appearance
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Names | |
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Preferred IUPAC name
1-Chloro-2-(2-chloroethane-1-sulfonyl)ethane | |
Other names
Bis(2-chloroethyl) sulfone, mustard sulfone, Yperite sulfone, H sulfone
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChemCID
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UNII | |
CompTox Dashboard(EPA)
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Properties | |
C4H8Cl2O2S | |
Molar mass | 191.07g·mol−1 |
Melting point | 52 °C (126 °F; 325 K) |
Solubility | ethanol; ether; chloroform |
Hazards | |
GHSlabelling: | |
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Danger | |
H301,H312 | |
P264,P270,P280,P301+P310,P302+P352,P312,P321,P322,P330,P363,P405,P501 | |
Related compounds | |
Related compounds
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mustard gas,mustard sulfoxide;Dibromodiethyl sulfone |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Dichlorodiethyl sulfone(ormustard sulfone) is an oxidation product ofmustard 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-transarrangement is predicted by Hartree-Fock computational methods to be the most stableconformer.[3]
Reactions[edit]
When refluxed with aqueous sodium hydroxide, oxygen replaces the chlorine, and an1,4-oxathianering 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]
- ^Lewis, Robert A. (2016).Hawley's Condensed Chemical Dictionary.John Wiley & Sons. p. 452.ISBN978-1-119-26784-3.
- ^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.
- ^abcBreslow, David S.;Skolnik, Herman (2009).Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles.John Wiley & Sons. p. 836.ISBN978-0-470-18833-0.