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Key Documents

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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Related Categories

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

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Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

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)
Christopher C Waller et al.
Steroids, 92, 74-80 (2014-10-07)
Steroid sulfates are a major class of steroid metabolite that are of growing importance in fields such as anti-doping analysis, the detection of residues in agricultural produce or medicine. Despite this, many steroid sulfate reference materials may have limited or

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