methyltrioxorhenium

• ChemBase ID: 148669
• Molecular Formular: CH3O3Re
• Molecular Mass: 249.23972
• Monoisotopic Mass: 249.96397196
• SMILES: C[Re](=O)(=O)=O
• Canonical SMILES: C[Re](=O)(=O)=O
• InChI: InChI=1S/CH3.3O.Re/h1H3
• InChIKey: PQTLALPZRPFYIT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyltrioxorhenium
• IUPAC Traditional name: methylrhenium trioxide
• Synonyms: MTO; Methylrhenium(VII) trioxide; Methyltrioxorhenium(VII); 甲基铼(VII)三氧化物; 甲基三氧化铼(VII)

Database IDs

• CAS Number: 70197-13-6
• MDL Number: MFCD00192332
• Beilstein Number: 3927932
• PubChem SID: 24885939; 162242844; 24865831
• PubChem CID: 2734010

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -1.0425
• LogD (pH = 7.4): -1.0425
• Log P: -1.0425
• Molar Refractivity: 9.654 cm^3
• Polarizability: 11.727564 Å^3
• Polar Surface Area: 51.21 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 110-115°C; 111 °C(lit.); 112-113 °C

Safety Information

• Storage Warning: Moisture & Light Sensitive
• European Hazard Symbols: Oxidising (O)
• UN Number: UN1479
• German water hazard class: 3
• Hazard Class: 5.1
• Packing Group: II
• Risk Statements: 8
• Safety Statements: 17-26-39
• TSCA Listed: 否
• GHS Pictograms: GHS03
• GHS Hazard statements: H272
• GHS Precautionary statements: P221-P210-P220-P280-P370+P378A-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (gas-volumetric); 98%
• Grade: purum
• Compostion: Re, 71.0-76.0%
• Linear Formula: CH3ReO3

DETAILS

Sigma Aldrich - 412910

Packaging
100, 500 mg in glass bottle
2 g in glass bottle
Application
Potent catalytic oxidant1,2 for converting alkenes to epoxides in a variety of solvents3 and 2-methylnaphthalene to 2-methyl-1,4-naphthoquinone (Vitamin K3).4,5Catalytic oxidant used with urea hydrogen peroxide in an efficient conversion of imines to nitrones.6An effective antioxidant under various conditions.7,8,9

Sigma Aldrich - 69489

Other Notes
Versatile and efficient catalyst soluble in water and organic solvents; e.g. olefin oxidation, olefin metathesis 1,2

REFERENCES

• For a brief feature on uses in synthesis, see: Synlett, 1849 (2004).
• Useful catalyst, soluble in organic solvents and water, and stable to air and acids: J. Organomet. Chem., 372, 351 (1989). Investigated by Herrmann's group as an alkene metathesis catalyst: Angew. Chem. Int. Ed., 30, 1636 (1991), a catalyst for clean epoxidation of alkenes with H₂O₂: Angew. Chem. Int. Ed., 30, 1638 (1991), and to promote the olefination of aldehydes with diazo esters: Angew. Chem. Int. Ed., 30, 1641 (1991). The activation of H₂O₂ in epoxidation and other reactions has been extensively studied; feature article: Chem. Commun., 479 (1999). Improved results in epoxidations with H₂O₂ in the presence of pyrazole have been reported by Herrmann: J. Organomet. Chem., 555, 293 (1998), and by Sharpless with pyrazole, pyridine or 3-cyanopyridine: Tetrahedron Lett., 40, 3991 (1999); J. Org. Chem., 65, 8651 (2000); see also Tetrahedron Lett., 39, 8521 (1998). For use in the Baeyer-Villiger oxidation of ketones, see: Angew. Chem. Int. Ed., 37, 1198 (1998); the reaction can also be carried out with H₂O₂ in ionic liquids at room temperature: Tetrahedron Lett., 44, 8991 (2003). Catalyzes the oxidative cleavage of ɑ-hydroxy carbonyl compounds to carboxylic acids with H₂O₂: Synth. Commun., 33, 3875 (2003). High yield aerobic oxidation of various organonitrogen compounds has been described: e.g. pyridines to N-oxides, anilines to nitrobenzenes and sec-amines to nitrones: Tetrahedron Lett., 44, 3235 (2003).