1,3-Propane sultone

1,3-Propane sultone
Names
IUPAC name
Oxathiolane 2,2-dioxide
Other names
γ-Propane sultone; 1,2-Oxathiolane, 2,2-dioxide; 3-Hydroxyl-1-propane sulfonic acid sulfone; 1-Propane sulfonic acid-3-hydroxyl-γ-sultone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.017
Properties
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 (88 °F; 304 K)
Boiling point 112 °C (234 °F; 385 K) at 1.4 mm Hg
10% (20°C)[1]
Hazards
Safety data sheet NIH.gov
Flash point 158 °C (316 °F; 431 K)
US health exposure limits (NIOSH):
PEL (Permissible)
 none[1]
REL (Recommended)
 Ca[1]
IDLH (Immediate danger)
 Ca [N.D.][1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[2][3] 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 hydroxysulfonic acid.

It has been used in the synthesis of specialist surfactants, such as CHAPS detergent.[4]

Safety

Typical of activated esters, 1,3-propane sultone is an alkylating agent. 1,3-Propane sultone is toxic, carcinogenic, mutagenic, and teratogenic.[5][6]

See also

References

  1. 1 2 3 4 "NIOSH Pocket Guide to Chemical Hazards #0525". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ R. J. Cremlyn (1996). An Introduction to Organosulfur Chemistry. Chichester: John Wiley and Sons. ISBN 0 471 95512 4.
  3. ↑ "Chem. Commun. article" (PDF). Retrieved 2008-11-17.
  4. ↑ Hjelmeland, LM (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. 77 (11): 6368–70. PMC 350285 Freely accessible. PMID 6935651. doi:10.1073/pnas.77.11.6368.
  5. ↑ "Scorecard Chemical Profile for Propane Sultone". Retrieved 2008-11-17.
  6. ↑ "NIOSH Pocket Guide to Chemical Hazards". Retrieved 2013-11-13.
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