pyridine; sulfonylideneoxidane

• ChemBase ID: 105455
• Molecular Formular: C5H5NO3S
• Molecular Mass: 159.1631
• Monoisotopic Mass: 158.99901403
• SMILES: O=S(=O)=O.c1ccncc1
• Canonical SMILES: c1cccnc1.O=S(=O)=O
• InChI: InChI=1S/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H
• InChIKey: UDYFLDICVHJSOY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pyridine; sulfonylideneoxidane
• IUPAC Traditional name: pyridine; sulfur trioxide
• Synonyms: NSC 75831; Pyridine sulfur trioxide complex; Sulfur trioxide pyridine complex; Sulfur Trioxide-Pyridine; Pyridine-Sulfur Trioxide Complex; Pyridine sulfur trioxide; SULFUR TRIOXIDE-PYRIDINE COMPLEX; Pyridine-sulfur trioxide complex; Sulfur trioxide-pyridine complex; 吡啶三氧化硫络合物; 三氧化硫吡啶络合物; 三氧化硫吡啶络合物,98%, 活性 SO

Database IDs

• CAS Number: 26412-87-3
• EC Number: 247-683-3
• MDL Number: MFCD00012437
• Beilstein Number: 3704116
• PubChem SID: 24888262; 162092553; 24899756
• PubChem CID: 168533

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.6230428
• LogD (pH = 7.4): 0.75354445
• Log P: 0.7555734
• Molar Refractivity: 23.9011 cm^3
• Polarizability: 9.4423685 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: ~160 °C; 155°C; 156-162°C; ca 155-165°C

Safety Information

• Storage Condition: 2-8°C; Refrigerator, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); X; Irritant (Xi)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 22-34; R:36/37/38
• Safety Statements: 20-26-36/37/39-45; 26-36/37/39-45; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H314-H318; H302-H314
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-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: ≥45% SO3 basis; 98%; 98%, active SO3 ca 48-50%
• Grade: technical
• Ignition Residue: ≤0.05%
• Empirical Formula (Hill Notation): C5H5NO3S

DETAILS

MP Biomedicals - 02190273

(Pyridine sulfur trioxide)

Sigma Aldrich - S7556

Packaging
25, 100 g in glass bottle
Application

• Sulfation agent1Reactant for:
• Preparation of azido anologs of pregnanolone2
• Sulfate esters of morphine derivatives3
• Gold nanoparticles capped with sulfate-ended ligands as anti-HIV agents4

Sigma Aldrich - 84737

Other Notes
Reagent used for sulfations of alcohols, sulfonations, deoxygenations and other reductions, oxidations with DMSO5,6,7
Packaging
10, 100, 500 g in glass bottle
Application

• Sulfation agent1Reactant for:
• Preparation of azido anologs of pregnanolone2
• Sulfate esters of morphine derivatives3
• Gold nanoparticles capped with sulfate-ended ligands as anti-HIV agents4

Toronto Research Chemicals - P991560

Pyridine-Sulfur Trioxide Complex is used in the sulfation of squid ink polysaccharides (SIPs) as a potential candidate compound for the prevention of tumor metastasis. Pyridine-Sulfur Trioxide Complex is also used in the preparation and anticoagulation te

REFERENCES

• Chen, S. et al.: Carb. Polymers, 81, 560 (2010)
• Li, S. et al.: Canya Kexue, 36, 553 (2010)
• 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).