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330744

Sigma-Aldrich

Tetrapropylammonium perruthenate

97%

Sinonimo/i:

TPAP

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About This Item

Formula condensata:
(CH3CH2CH2)4NRuO4
Numero CAS:
Peso molecolare:
351.43
Numero MDL:
Codice UNSPSC:
12352116
ID PubChem:
NACRES:
NA.22

Saggio

97%

Forma fisica

solid

Impiego in reazioni chimiche

reagent type: oxidant

Punto di fusione

~160 °C (dec.) (lit.)

Stringa SMILE

[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;
NQSIKKSFBQCBSI-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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


Certificati d'analisi (COA)

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Tetrapropylammonium Perruthenate, Pr4N+RuO4 -, TPAP: A Catalytic Oxidant for Organic Synthesis
Steven V.L, et al.
Synthesis, 7, 639-666 (1994)
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
Aldrichimica Acta, 23, 13-13 (1990)
Single and multiphase catalytic oxidation of benzyl alcohol by tetrapropylammonium perruthenate in a mobile microreactor system
Cao E, et al.
Chemical Engineering & Technology, 29(11), 1372-1375 (2006)
Tetrapropylammonium perruthenate, Pr4N+ RuO4-, TPAP: A catalytic oxidant for organic synthesis
Ley Steven V, et al.
Synthesis, 1994(07), 639-666 (1994)

Articoli

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

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