Sultone

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1,3-Propane sultone
1,3-Propane sultone
Identifiers
CAS number 1120-71-4 YesY
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)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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]

Hydrolysis of Propane-1,3-sultone

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[edit]

References[edit]