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Merck

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

Quality Level

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.[1][2]

Application

Tetrapropylammonium perruthenate (TPAP) can be used as a catalyst:     
  • For the conversion of sulfides to sulfones by oxidation reaction.[2]       
  • In the isomerization of allylic alcohols into the corresponding saturated carbonyl derivatives.[3]      
  •  Along with N-methylmorpholine N-oxide (NMO) for the cleavage of glycol to carboxylic acids.[4]

TPAP can also be used as an oxidizing reagent:
  • For the oxidation of benzyl alcohol to benzaldehyde and steroidal alcohols to corresponding ketones.[5][6]
  • To convert N,N′-dihydroxyimidazolidines to nitronyl nitroxide free radicals.[7]
  • To oxidize hydroxyl-substituted tri-n-butylammonium trifluoroborates to aldehydes and ketones without concomitant cleavage of the carbon-boron bond.[8][9]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Tetrapropylammonium perruthenate catalyzed glycol cleavage to carboxylic (di) acids
Schmidt A-KC and Stark CBW
Organic Letters, 13(21), 5788-5791 (2011)
Synthesis, 639-639 (1994)

Articles

Oxidation and reduction reactions are some of the most common transformations encountered in organic synthesis, and are some of the organic chemist’s most powerful tools for creating novel products. Below is a list of the most commonly used oxidizing and reducing agents currently available in our catalog.

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