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1,3-Propane sultone

1,3-Propane sultone is the organosulfur compound with the formula (CH2)3SO3. It is a cyclic sulfonate ester, a class of compounds called sultones. It is a readily melting colorless solid.

Synthesis

It may be prepared by the acid catalyzed reaction of allyl alcohol and sodium bisulfite.

Reactions

1,3-propane sultone is an activated ester and is susceptible to nucleophilic attack. It hydrolyzes to the 3-hydroxypropylsulfonic acid.

:[[File:Propane-1,3-sultone hydrolysis.svg|400px|Hydrolysis of Propane-1,3-sultone]]

It has been used in the synthesis of specialist surfactants, such as CHAPS detergent.

Safety

Typical of activated esters, 1,3-propane sultone is an alkylating agent. 1,3-Propane sultone is toxic, carcinogenic, mutagenic, and teratogenic.

References

References

  1. {{PGCH. 0525
  2. R. J. Cremlyn. (1996). "An Introduction to Organosulfur Chemistry". John Wiley and Sons.
  3. (2000). "Can α-sultone exist as a chemical species? First experimental implication for intermediacy of α-sultone". Chemical Communications.
  4. (November 1980). "A nondenaturing zwitterionic detergent for membrane biochemistry: design and synthesis.". Proceedings of the National Academy of Sciences of the United States of America.
  5. "Scorecard Chemical Profile for Propane Sultone".
  6. "NIOSH Pocket Guide to Chemical Hazards".
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