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.[2][3] It is a readily melting colorless solid.

1,3-Propane sultone
1,3-Propane sultone
Names
Preferred IUPAC name
1,2λ6-Oxathiolane-2,2-dione
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; Oxathiolane 2,2-dioxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.017
UNII
  • InChI=1S/C3H6O3S/c4-7(5)3-1-2-6-7/h1-3H2
    Key: FSSPGSAQUIYDCN-UHFFFAOYSA-N
  • InChI=1/C3H6O3S/c4-7(5)3-1-2-6-7/h1-3H2
    Key: FSSPGSAQUIYDCN-UHFFFAOYAH
  • C1COS(=O)(=O)C1
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
Flash point 158 °C (316 °F; 431 K)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 Ca[1]
IDLH (Immediate danger)
 Ca [N.D.][1]
Safety data sheet (SDS) NIH.gov
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

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.

Hydrolysis of Propane-1,3-sultone

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. 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. Morimoto, Yoshiki; Kurihara, Hajime; Kinoshita, Takamasa (2000). "Can α-sultone exist as a chemical species? First experimental implication for intermediacy of α-sultone" (PDF). Chemical Communications (3): 189–190. doi:10.1039/A909094K.
  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. Bibcode:1980PNAS...77.6368H. doi:10.1073/pnas.77.11.6368. PMC 350285. PMID 6935651.
  5. "Scorecard Chemical Profile for Propane Sultone". Archived from the original on 2008-09-23. Retrieved 2008-11-17.
  6. "NIOSH Pocket Guide to Chemical Hazards". Retrieved 2013-11-13.
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