Sultone
| 1,3-Propane sultone | ||
|---|---|---|
 | ||
| IUPAC name 1,3-Propane sultone | ||
| Other names γ-Propane sultone; 1,2-Oxathiolane, 2,2-dioxide (9CI); 3-Hydroxyl-1-propane sulfonic acid sulfone; 1-Propane sulfonic acid-3-hydroxyl-γ-sultone | ||
| Identifiers | ||
| CAS number | 1120-71-4  | |
| Properties | ||
| Molecular formula | C3H6O3S | |
| Molar mass | 122.14 g mol−1 | |
| Appearance | White crystalline solid, colorless liquid above 31 °C | |
| Density | 1.392 g/cm3 at 40 °C | |
| Melting point | 31 °C | |
| Boiling point | 112 °C at 1.4 mm Hg | |
| Hazards | ||
| MSDS | NIH.gov | |
| Flash point | 158 °C; 316 °F; 431 K | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
In organic chemistry, sultones are cyclic sulfonate esters of hydroxy sulfonic acids that exist mainly as four-, seven-, and sometimes five-membered rings.[1] They are often short-lived intermediates, used as strong alkylating agents to introduce a negatively charged sulfonate group.
In the presence of water, they slowly hydrolyze to their respective corrosive hydroxy sulfonic acids. Sultones decompose when heated to produce toxic, foul smelling, sulfur dioxide fumes.[2][3]
Sultone oximes are key intermediates in the synthesis of the anti-convulsant drug zonisamide.[4]
Sultones are classified as toxic, carcinogenic, mutagenic, and teratogenic.[5][6]
See also
References
- ↑ "Chem. Commun. article". Retrieved 2008-11-17.
- ↑ "Inchem.org Safety Data Sheet". Retrieved 2008-11-17.
- ↑ "NOAA.gov chemical data sheet". Retrieved 2008-11-17.
- ↑ "Arava, V.R., et al. "Novel base catalysed rearrangement of sultone oximes." Beilstein J. Org. Chem., 2007, 3(20)".
- ↑ "Scorecard Chemical Profile for Propane Sultone". Retrieved 2008-11-17.
- ↑ "NIOSH Pocket Guide to Chemical Hazards". Retrieved 2013-11-13.