Sulfur trioxide-pyridine complex, 98%, active SO3 ca 48-50%

Name: Sulfur trioxide-pyridine complex, 98%, active SO3 ca 48-50%
SKU: A12202.09

CAS: 26412-87-3 | C5H5NO3S | 159.16 g/mol

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Catalog number A12202.09

also known as A12202-09

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Chemical Identifiers

CAS26412-87-3

IUPAC Namepyridine; sulfonylideneoxidane

Molecular FormulaC5H5NO3S

InChI KeyUDYFLDICVHJSOY-UHFFFAOYSA-N

SMILESO=S(=O)=O.C1=CC=NC=C1

Specifications

Specification Sheet

Appearance (Color)White to cream to pale brown or pale yellow

Assay (Aqueous acid-base Titration)≥97.5 to ≤102.5%

Identification (FTIR)Conforms

FormPowder

Sulfur trioxide-pyridine complex is used for sulfations of alcohols, sulfonations, deoxygenations and other reductions, oxidations with dimethyl sulfoxide. It is also used as a source of sulfur trioxide especially in the preparation of sulfate esters. Further, it is used as an activating electrophile in a Parikh-Doering oxidation. In addition to this, it is also used in the preparation and anticoagulation test of sulfated silk fibroin.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Sulfur trioxide-pyridine complex is used for sulfations of alcohols, sulfonations, deoxygenations and other reductions, oxidations with dimethyl sulfoxide. It is also used as a source of sulfur trioxide especially in the preparation of sulfate esters. Further, it is used as an activating electrophile in a Parikh-Doering oxidation. In addition to this, it is also used in the preparation and anticoagulation test of sulfated silk fibroin.

Solubility
Soluble in polar organic solvents.

Notes
Moisture sensitive. Incompatible with strong oxidizing agents.

RUO – Research Use Only

General 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).
Sulfonates indole at the 3-position: Tetrahedron, 29, 669 (1973).
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°C to convert an epoxy alcohol to the corresponding aldehyde in the synthesis of hemibrevitoxin B: J. Am. Chem. Soc., 115, 3558 (1993).
In combination with NaI, reduces ɑ-halo ketones to ketones: Synthesis, 59 (1979), and sulfoxides to sulfides: Synthesis, 984 (1979).
Lim, D. K.; Wylie, R. G.; Langer, R.; Kohane, D. S. Selective binding of C-6 OH sulfated hyaluronic acid to the angiogenic isoform of VEGF₁₆₅. Biomaterials 2016, 77, 130-138.
Sarbova, V.; Koschella, A.; Cheng, F.; Kelly, S. M.; Heinze, T. Studies on the sulfation of cellulose alpha-lipoate and ability of the sulfated product to stabilize colloidal suspensions of gold nanoparticles. Carbohydr. Polym. 2015, 124, 117-123.