[(methoxymethyl)(phenyl)phosphoroso]benzene

• ChemBase ID: 149515
• Molecular Formular: C14H15O2P
• Molecular Mass: 246.241461
• Monoisotopic Mass: 246.08096635
• SMILES: COCP(=O)(c1ccccc1)c1ccccc1
• Canonical SMILES: COCP(=O)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C14H15O2P/c1-16-12-17(15,13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-11H,12H2,1H3
• InChIKey: OEPKDBQOTLDTNC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(methoxymethyl)(phenyl)phosphoroso]benzene
• IUPAC Traditional name: [methoxymethyl(phenyl)phosphoroso]benzene
• Synonyms: Diphenyl(methoxymethyl)phosphine oxide; (Methoxymethyl)diphenylphosphine oxide; 二苯基(甲氧基甲基)氧化膦; (甲氧基甲基)二苯基氧化膦; ( 甲氧基甲基)二苯基磷氧

Database IDs

• CAS Number: 4455-77-0
• EC Number: 224-704-4
• MDL Number: MFCD00015451
• Beilstein Number: 649558
• PubChem SID: 24866971; 162243680; 24868881
• PubChem CID: 78203

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.3126
• LogD (pH = 7.4): 3.3126
• Log P: 3.3126
• Molar Refractivity: 69.328 cm^3
• Polarizability: 27.714018 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methylene chloride: soluble0.1 g/mL, clear
• Melting Point: 114-120°C; 115-117 °C; 115-117 °C(lit.)

Safety Information

• RTECS: SZ0199360
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 22-36/37/38
• Safety Statements: 26-36/37-60
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• GHS Precautionary statements: P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (CH); 98%; 98+%
• Grade: purum
• Linear Formula: (C6H5)2P(O)CH2OCH3

DETAILS

Sigma Aldrich - 454087

Packaging
10 g in glass bottle
Application
Catalyst for:
• Molybdenum hexacarbonyl-mediated Pauson-Khand reactions1
• Rhodium-catalyzed hydroformylation reaction2

Sigma Aldrich - 43115

Other Notes
Horner-Wittig reagent for the preparation of methyl vinyl ethers3,4,5,6
Application
Catalyst for:
• Molybdenum hexacarbonyl-mediated Pauson-Khand reactions1
• Rhodium-catalyzed hydroformylation reaction2

REFERENCES

• Horner olefination with aldehydes and ketones gives vinyl ethers (and hence higher aldehydes). The method is reported to be superior to the Wittig alternative. The two diastereoisomeric adducts can also be isolated and each converted to a single stereoisomer of the enol ether: J. Chem. Soc., Perkin 1, 3099 (1979):