Chemistry:Dichlorodiethyl sulfone
From HandWiki
Short description: Oxidation product of mustard gas
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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 | |
PubChem CID
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| UNII | |
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| Properties | |
| C4H8Cl2O2S | |
| Molar mass | 191.07 g·mol−1 |
| Melting point | 52 °C (126 °F; 325 K) |
| Solubility | ethanol; ether; chloroform |
| Hazards | |
| GHS pictograms |  
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| GHS Signal word | Danger |
| H301, H312 | |
| P264, P270, P280, P301+310, P302+352, 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 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) (in en). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. p. 452. ISBN 978-1-119-26784-3. https://books.google.com/books?id=KPrfCwAAQBAJ&pg=PA452.
- ↑ (in en) Transactions of the Annual Conference of State Sanitary Engineers. 1943. p. 3–175. https://books.google.com/books?id=8zSpqSJSC00C&pg=RA3-PA175.
- ↑ 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.
- ↑ 4.0 4.1 4.2 Breslow, David S.; Skolnik, Herman (2009) (in en). Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles. John Wiley & Sons. p. 836. ISBN 978-0-470-18833-0. https://books.google.com/books?id=CgRLJvZYBpYC&pg=PA836.
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