tetrapropylazanium rutheniumoylolate

• ChemBase ID: 129811
• Molecular Formular: C12H28NO4Ru
• Molecular Mass: 351.42502
• Monoisotopic Mass: 352.10618238
• SMILES: CCC[N+](CCC)(CCC)CCC.O=[Ru](=O)(=O)[O-]
• Canonical SMILES: [O-][Ru](=O)(=O)=O.CCC[N+](CCC)(CCC)CCC
• InChI: 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
• InChIKey: NQSIKKSFBQCBSI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrapropylazanium rutheniumoylolate
• IUPAC Traditional name: tetrapropylammonium rutheniumoylolate
• Synonyms: TPAP; Tetrapropylammonium perruthenate; Tetrapropylammonium perruthenate; Tetra-n-propylammonium perruthenate(VII); 四丙基高钌酸铵; 四正丙基过钌(VII)酸铵

Database IDs

• CAS Number: 114615-82-6
• MDL Number: MFCD00074914
• PubChem SID: 24889060; 24859883
• Wikipedia Title: Tetrapropylammonium_perruthenate

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -0.45484576
• LogD (pH = 7.4): -0.45484576
• Log P: -0.45484576
• Molar Refractivity: 72.9921 cm^3
• Polarizability: 24.346558 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Green solid
• Melting Point: ~160 °C (dec.)(lit.); 160 °C (decomposition); 160°C dec.

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: Oxidising (O); Irritant (Xi)
• UN Number: 1479; UN1479
• German water hazard class: 3
• Hazard Class: 5.1
• Packing Group: 2; III
• Risk Statements: 5-8-36/37/38
• Safety Statements: 17-26-36; 17-26-37
• TSCA Listed: 否
• GHS Pictograms: GHS03; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H272-H315-H319-H335
• GHS Precautionary statements: P220-P261-P305 + P351 + P338; P221-P210-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1479 5.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%
• Grade: purum
• Linear Formula: (CH3CH2CH2)4NRuO4

DETAILS

Sigma Aldrich - 330744

Application
A soluble, nonvolatile, air-stable, mild oxidant which can be used either stoichiometrically or catalytically with a suitable co-oxidant.
Oxidant used to convert N,N′-dihydroxyimidazolidines to nitronyl nitroxide free radicals.1 Oxidation of hydroxyl-substituted tri-n-butylammonium trifluoroborates to aldehydes and ketones without concomitant cleavage of the carbon-boron bond.2,3
Packaging
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 88126

Other Notes
Catalyst for the mild N-methylmorpholine N-oxide, NMO, mediated oxidation of alcohols to carbonyl compounds in methylene chloride1

REFERENCES

• For a brief feature on uses in synthesis, see: Synlett, 824 (2007).
• Selective, catalytic oxidant introduced by Ley. Normally used in combination with N-methylmorpholine-N-oxide as the stoichiometric reoxidant and 4A molecular sieves to remove water. Preferred solvents are dichloromethane and acetonitrile. Primary and secondary alcohols are oxidized to aldehydes and ketones in high yield: J. Chem. Soc., Chem. Commun., 1625 (1987). For an example of alcohol to aldehyde oxidation in the partial synthesis of the acyl tetronic acid ionophore tetronasin, see: Tetrahedron Lett., 35, 319 (1994). Also useful for a number of other oxidations such as lactols to lactones and sulfides to sulfones. For oxidation of secondary amines to imines, and of hydroxylamines to nitrones, see: Tetrahedron Lett., 35, 6567, 6571 (1994).
• For a comprehensive review of this reagent, see: Synthesis, 639 (1994). For a review of ruthenium oxo-complexes as organic oxidants, see: Chem. Soc. Rev., 21, 179 (1992).