sulfonylideneoxidane; trimethylamine

• ChemBase ID: 89796
• Molecular Formular: C3H9NO3S
• Molecular Mass: 139.17346
• Monoisotopic Mass: 139.03031415
• SMILES: N(C)(C)C.S(=O)(=O)=O
• Canonical SMILES: CN(C)C.O=S(=O)=O
• InChI: InChI=1S/C3H9N.O3S/c2*1-4(2)3/h1-3H3
• InChIKey: DXASQZJWWGZNSF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfonylideneoxidane; trimethylamine
• IUPAC Traditional name: sulfur trioxide; trimethylamine
• Synonyms: NSC 9838; Trimethylamine sulfur trioxide complex; Sulfur trioxide trimethylamine complex; Trimethylamine sulphur trioxide complex; Sulphur trioxide trimethylamine complex 95%; Trimethylamine-sulfur trioxide complex; Sulfur trioxide-trimethylamine complex; 硫磺三氧三甲胺联合体; 三甲基铵三氧化硫共聚物; 三氧化硫三甲胺复合物

Database IDs

• CAS Number: 3162-58-1
• EC Number: 221-614-7
• MDL Number: MFCD00012421
• Beilstein Number: 3681759
• PubChem SID: 24848242; 162076652
• PubChem CID: 222852

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -3.208248
• LogD (pH = 7.4): -1.966536
• Log P: 0.19016947
• Molar Refractivity: 19.9881 cm^3
• Polarizability: 7.800994 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 232 °C (dec.)(lit.); 232(dec.)°C; ca 235°C dec.

Safety Information

• Storage Warning: Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: 95%
• Linear Formula: (CH3)3N · SO3

DETAILS

Sigma Aldrich - 135879

Packaging
5, 100, 500 g in glass bottle
Application
Reactant for sulfation reactions involving:
• Synthesis of sulfate-conjugated resveratrol metabolites1
• Chitooligosaccharides used for anti-HIV-1 activity2
• Dodecyl thioglycopyranoside used as a surfactant for enantiomeric separation3
• Glycosaminoglycans which facilitate activation of signaling pathways dependent on sulfation pattern4
• Polysaccharides as heparan sulfate mimetics5Nucleophile for the synthesis of α-tosyloxy ketones6

REFERENCES

• 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):
  
• 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).