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S7556

Sigma-Aldrich

Sulfur trioxide pyridine complex

97%

Synonym(s):

NSC 75831, Pyridine sulfur trioxide complex

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About This Item

Empirical Formula (Hill Notation):
C5H5NO3S
CAS Number:
Molecular Weight:
159.16
Beilstein:
3704116
EC Number:
MDL number:
UNSPSC Code:
12352303
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

reaction suitability

reagent type: oxidant

SMILES string

O=S(=O)=O.c1ccncc1

InChI

1S/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H;

InChI key

UDYFLDICVHJSOY-UHFFFAOYSA-N

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Application

  • Sulfation agent

Reactant for:
  • Preparation of azido anologs of pregnanolone
  • Sulfate esters of morphine derivatives
  • Gold nanoparticles capped with sulfate-ended ligands as anti-HIV agents
Sulfur trioxide-pyridine (SO3-py) complex can be used to convert the allylic or benzylic hydroxyl group of compounds such as geraniol, farnesol, and 1-indanol into sulfate monoester, which is a good leaving group. This method is highly useful in the total synthesis of sesquiterpenes.
As a sulfating agent, SO3-py complex can be used for the preparation of sulfated-chitins, sulfated hyaluronan (HyaS) derivatives and sulfated starch.

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Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Polysaccharide-based superporous hydrogels with fast swelling and superabsorbent properties.
Kuang J, et al.
Carbohydrate Polymers, 83(1), 284-290 (2011)
A method for deoxygenation of allylic and benzylic alcohols.
Corey E J and Achiwa K
The Journal of Organic Chemistry, 34(11), 3667-3668 (1969)
Preparation of sulfated-chitins under homogeneous conditions.
Zou Y and Khor E
Carbohydrate Polymers, 77(3), 516-525 (2009)
Sulfated hyaluronan derivatives reduce the proliferation rate of primary rat calvarial osteoblasts.
Kunze R, et al.
Glycoconjugate Journal, 27(1), 151-158 (2010)
Helyn Priscila de Oliveira Barddal et al.
International journal of biological macromolecules, 145, 604-610 (2019-12-31)
Heparin is an extremely important and recognized anticoagulant and antithrombotic agent. Obtained from animal sources and being highly potent, risks of contamination by pathogens and bleeding are some concerns related to heparin use. In the search for alternatives to heparin

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