1,3-Propane sultone

changed 442825188 1,3-Propane sultone Propio-1,3-sultone.svg 110px 1,3-Propane sultone 1,2λ6-Oxathiolane-2,2-dione 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 correct CAS 1120-71-4 correct FDA L6NTK7VJX9 C1COS(=O)(=O)C1 14264 13626 1/C3H6O3S/c4-7(5)3-1-2-6-7/h1-3H2 FSSPGSAQUIYDCN-UHFFFAOYAH 1S/C3H6O3S/c4-7(5)3-1-2-6-7/h1-3H2 FSSPGSAQUIYDCN-UHFFFAOYSA-N 3 6 3 1 1.392 g/cm3 at 40 °C 31 112 at 1.4 mm Hg White crystalline solid; colorless liquid above 31 °C 10% (20°C) NIH.gov 158 Ca [N.D.]0525 Ca none 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. R. J. Cremlyn An Introduction to Organosulfur Chemistry John Wiley and Sons Chichester 1996 0-471-95512-4Morimoto Yoshiki Kurihara Hajime Kinoshita Takamasa Can α-sultone exist as a chemical species? First experimental implication for intermediacy of α-sultone http://www.rsc.org/ej/CC/2000/a909094k.pdf Chemical Communications 2000 3 189–190 10.1039/A909094K 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. 400px|class=skin-invert-image|Hydrolysis of Propane-1,3-sultone It has been used in the synthesis of specialist surfactants, such as CHAPS detergent.Hjelmeland LM A nondenaturing zwitterionic detergent for membrane biochemistry: design and synthesis. Proceedings of the National Academy of Sciences of the United States of America November 1980 77 11 6368–70 6935651 10.1073/pnas.77.11.6368 350285 1980PNAS...77.6368H free Safety Typical of activated esters, 1,3-propane sultone is an alkylating agent. 1,3-Propane sultone is toxic, carcinogenic, mutagenic, and teratogenic.http://www.scorecard.org/chemical-profiles/summary.tcl?edf_substance_id=1120-71-4#hazards Scorecard Chemical Profile for Propane Sultone 2008-11-17 2008-09-23 https://web.archive.org/web/20080923100823/http://www.scorecard.org/chemical-profiles/summary.tcl?edf_substance_id=1120-71-4#hazards deadhttps://www.cdc.gov/niosh/npg/npgd0525.html NIOSH Pocket Guide to Chemical Hazards 2013-11-13 See also 1,4-Butane sultone Dimethyl sulfate Vinylsulfonic acid Isethionic acid Sulfolane References 30em Category:Sultones Category:IARC Group 2A carcinogens