Sulfur trioxide-pyridine complex

• Catalog No.: A12202
• CAS Number: 26412-87-3
• M. F.: C5H5NO3S
• M. W.: 159.1631
• Purity: 98%, active SO3 ca 48-50%

SYNONYMS

• Title: 三氧化硫吡啶络合物,98%, 活性 SO
• IUPAC name: pyridine; sulfonylideneoxidane
• IUPAC Traditional name: pyridine; sulfur trioxide
• Synonyms: Pyridine-sulfur trioxide complex

DATABASE IDS

• EC Number: 247-683-3
• MDL Number: MFCD00012437
• CAS Number: 26412-87-3
• Beilstein Number: 3704116

PROPERTIES

• Purity: 98%, active SO3 ca 48-50%
• Melting Point: ca 155-165°C
• GHS Hazard statements: H301-H314-H318
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 22-34
• Safety Statements: 20-26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: II

REFERENCES

• Converts alcohols to monoalkyl sulfates, utilized in carbohydrate protection: Carbohydr. Res., 127, 211, 131, C8 (1984); J. Org. Chem., 38, 3510 (1973). The pyridinium sulfates of allylic or benzylic alcohols can be deoxygenated in high yields by in situ LiAlH₄ reduction in THF: J. Org. Chem., 34, 3667 (1969); Tetrahedron Lett., 4650 (1972); J. Am. Chem. Soc., 93, 7016 (1971).
• The combination with Dimethyl sulfoxide, A13280, is a mild oxidant for alcohols to carbonyl compounds (Parikh-Doering Reagent): J. Am. Chem. Soc., 89, 5505 (1967), avoiding the very low temperatures required for the Swern and similar systems (see Oxalyl chloride, A18012). With chiral alcohols, less racemization occurs at the ɑ-carbon than with Collins' reagent or pyridinium dichromate: Tetrahedron Lett., 23, 807 (1982); J. Org. Chem., 46, 4799 (1981). Nicolaou utilized the system at 0^oC to convert an epoxy alcohol to the corresponding aldehyde in the synthesis of hemibrevitoxin B: J. Am. Chem. Soc., 115, 3558 (1993).
• Sulfonates indole at the 3-position: Tetrahedron, 29, 669 (1973).
• In combination with NaI, reduces ɑ-halo ketones to ketones: Synthesis, 59 (1979), and sulfoxides to sulfides: Synthesis, 984 (1979).