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330744

Sigma-Aldrich

Tetrapropylammonium perruthenate

97%

Synonym(s):

TPAP

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About This Item

Linear Formula:
(CH3CH2CH2)4NRuO4
CAS Number:
Molecular Weight:
351.43
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

solid

reaction suitability

reagent type: oxidant

mp

~160 °C (dec.) (lit.)

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


Certificates of Analysis (COA)

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Ulyana Munoz Acuña et al.
Anticancer research, 37(4), 1617-1623 (2017-04-05)
The survival rate of women diagnosed with triple-negative breast-cancer (TNBC) remains low. Hence, this study aimed at the chemical and biological optimization of furanosteroid derivatives for the treatment of this type of malignancy using TNBC cells. Semi-synthetic analogs of wortmannolone
TPAP/NMO System as a Novel Method for the Synthesis of Nitronyl Nitroxide Radicals
Lapo Gorini, et al.
Synlett, 6, 948-950 (2006)
Synthesis, 639-639 (1994)
Novel and efficient isomerization of allylic alcohols promoted by a tetrapropylammonium perruthenate catalyst
Marko IE, et al.
Angewandte Chemie (International ed. in English), 38(13-14), 1960-1962 (1999)
Tetrapropylammonium perruthenate catalyzed glycol cleavage to carboxylic (di) acids
Schmidt A-KC and Stark CBW
Organic Letters, 13(21), 5788-5791 (2011)

Articles

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

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