1,3-Propane sultone

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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[edit]

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

Reactions[edit]

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

Hydrolysis of Propane-1,3-sultone

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

Safety[edit]

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[edit]

References[edit]

  1. ^ a b c d "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. doi:10.1073/pnas.77.11.6368. PMC 350285Freely accessible. PMID 6935651. 
  5. ^ "Scorecard Chemical Profile for Propane Sultone". Retrieved 2008-11-17. 
  6. ^ "NIOSH Pocket Guide to Chemical Hazards". Retrieved 2013-11-13.