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Merck

330744

Sigma-Aldrich

Tetrapropylammonium perruthenate

97%

Sinónimos:

TPAP

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About This Item

Fórmula lineal:
(CH3CH2CH2)4NRuO4
Número de CAS:
Peso molecular:
351.43
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

solid

reaction suitability

reagent type: oxidant

mp

~160 °C (dec.) (lit.)

functional group

amine

SMILES string

[O-][Ru](=O)(=O)=O.CCC[N+](CCC)(CCC)CCC

InChI

1S/C12H28N.4O.Ru/c1-5-9-13(10-6-2,11-7-3)12-8-4;;;;;/h5-12H2,1-4H3;;;;;/q+1;;;;-1;

InChI key

NQSIKKSFBQCBSI-UHFFFAOYSA-N

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General description

Tetrapropylammonium perruthenate is a mild oxidizing agent used for the oxidation of alcohols to corresponding carbonyl compounds. It is a non-volatile, air-stable, and readily soluble reagent, which can be used either stoichiometrically or catalytically with a suitable co-oxidant.

Application

Tetrapropylammonium perruthenate (TPAP) can be used as a catalyst:     
  • For the conversion of sulfides to sulfones by oxidation reaction.       
  • In the isomerization of allylic alcohols into the corresponding saturated carbonyl derivatives.      
  •  Along with N-methylmorpholine N-oxide (NMO) for the cleavage of glycol to carboxylic acids.

TPAP can also be used as an oxidizing reagent:
  • For the oxidation of benzyl alcohol to benzaldehyde and steroidal alcohols to corresponding ketones.
  • To convert N,N′-dihydroxyimidazolidines to nitronyl nitroxide free radicals.
  • To oxidize hydroxyl-substituted tri-n-butylammonium trifluoroborates to aldehydes and ketones without concomitant cleavage of the carbon-boron bond.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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Visite la Librería de documentos

Synthesis, 639-639 (1994)
Tetrahedron Letters, 45, 303-308 (2004)
Gary A Molander et al.
Journal of the American Chemical Society, 128(30), 9634-9635 (2006-07-27)
Potassium- and tetra-n-butylammonium organotrifluoroborates containing hydroxyl groups have been prepared and oxidized using several common oxidants. Aryl-, alkenyl-, and alkyltrifluoroborates containing both primary and secondary hydroxyl groups were oxidized in moderate to excellent yields with complete retention of the trifluoroborate
Tetrapropylammonium Perruthenate, Pr4N+RuO4 -, TPAP: A Catalytic Oxidant for Organic Synthesis
Steven V.L, et al.
Synthesis, 7, 639-666 (1994)
Aldrichimica Acta, 23, 13-13 (1990)

Artículos

Oxidation and reduction reactions are some of the most common transformations encountered in organic synthesis

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