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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: H302-H314
Harmful if swallowed. Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P270-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant