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Merck
CN

330744

Tetrapropylammonium perruthenate

97%

Synonym(s):

TPAP

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About This Item

Linear Formula:
(CH3CH2CH2)4NRuO4
CAS Number:
114615-82-6
Molecular Weight:
351.43
NACRES:
NA.22
PubChem Substance ID:
24859883
UNSPSC Code:
12352116
MDL number:
MFCD00074914
Assay:
97%
Form:
solid

Key Documents

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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;

SMILES string

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

InChI key

NQSIKKSFBQCBSI-UHFFFAOYSA-N

assay

97%

form

solid

reaction suitability

reagent type: oxidant

mp

~160 °C (dec.) (lit.)

functional group

amine

Quality Level

200

Related Categories

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.

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

pictograms

Flame over circleExclamation mark
GHS03,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Ox. Sol. 2 - Skin Irrit. 2

Storage Class

5.1B - Oxidizing hazardous materials

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ9548
STBG1237V
STBD8558V
STBD8557V
STBD8559V

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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)
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
Brooks E Maki et al.
Organic letters, 11(7), 1651-1654 (2009-03-27)
Indoles and alcohols can be coupled in a dehydrogenative process catalyzed by tetrapropylammonium perruthenate. This efficient approach to indolylamides proceeds in a single flask under mild conditions. By employing substituted indoles and alkyl, branched, or benzylic alcohols, a variety of
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Articles

Oxidizing and Reducing Agents

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

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