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Sulfur trioxide-trimethylamine complex acts as a reagent for sulfonation and sulfamation reactions. It is used as a reactant for the synthesis of sulfate-conjugated resveratrol metabolites and chitooligosaccharides. It is used in association with dodecyl thioglycopyranoside, which acts as a surfactant for enantiomeric separation. Further, it acts as a nucleophile used for the preparation of alfa-tosyloxy ketones.
Converts alcohols and phenols to their monosulfates under mild conditions: Ber., 57, 1045 (1924); J. Am. Chem. Soc., 74, 5212 (1952).
Reagent for the dehydration of oximes: Synthesis, 702 (1978).
Conditions have been described for the conversion of organolithiums in THF to sulfonic acids by insertion of SO3 into the C-Li bond: J. Org. Chem., 61, 1530 (1996):
Mans, D. J.; Ye, H.; Dunn, J. D.; Kolinski, R. E.; Long, D. S.; Phatak, N. L.; Ghasriani, H.; Buhse, L. F.; Kauffman, J. F.; Keire, D. A. Synthesis and detection of N-sulfonated oversulfated chondroitin sulfate in marketplace heparin. Anal. Biochem. 2015, 490, 52-54.
Jacquinet, J. C.; Lopin-Bon, C. Stereocontrolled preparation of biotinylated chondroitin sulfate E di-, tetra-, and hexasaccharide conjugates. Carbohydr. Res. 2015, 402, 35-43.
Hazard Statements: H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.