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75920

Sigma-Aldrich

OXONE® tetrabutylammonium salt

technical, ~1.6% active oxygen basis

Synonym(s):

Tetrabutylammonium OXONE®, Tetrabutylammonium hydrogen monopersulfate, Tetrabutylammonium peroxomonosulfate, Tetrabutylammonium persulfate triple salt

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About This Item

CAS Number:
104548-30-3
Beilstein:
5199887
UNSPSC Code:
12352000
PubChem Substance ID:
24886893
NACRES:
NA.22

grade

technical

form

powder

reaction suitability

reagent type: oxidant

concentration

~1.6% (active oxygen)

mp

144-146 °C

SMILES string

OS([O-])(=O)=O.[O-]S([O-])(=O)=O.OS(=O)(=O)O[O-].OS(=O)(=O)O[O-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/5C16H36N.2H2O5S.2H2O4S/c5*1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;2*1-5-6(2,3)4;2*1-5(2,3)4/h5*5-16H2,1-4H3;2*1H,(H,2,3,4);2*(H2,1,2,3,4)/q5*+1;;;;/p-5

InChI key

IGMBKNUVZFAHJM-UHFFFAOYSA-I

Application

Reagent for:
  • Oxidation of Hantzsch 1,4-Dihydropyridines catalyzed by manganese(III) Schiff Base complexes
  • Epoxidation of alkenes
  • Oxidation of sulfides and olefins
  • Oxidation of alcohols
  • Oxidation of aromatic amines for synthesis of azoxy arenes

Other Notes

Form of Oxone specially suited for the oxidation of sensitive compounds in CH2Cl2; Reagent for preparing 2-tetrahydrofuranyl ethers from alcohols and THF by radical coupling

Legal Information

OXONE is a registered trademark of E. I. du Pont de Nemours and Company

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R. Cosstick et al.
Tetrahedron Letters, 30, 4693-4693 (1989)
J.C. Jung et al.
Tetrahedron Letters, 34, 3581-3581 (1993)
B.M. Trost et al.
The Journal of Organic Chemistry, 53, 532-532 (1988)
R. Annunziata et al.
The Journal of Organic Chemistry, 55, 1901-1901 (1990)

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