[methyl(phenyl)phosphoroso]benzene

• ChemBase ID: 83016
• Molecular Formular: C13H13OP
• Molecular Mass: 216.215481
• Monoisotopic Mass: 216.07040167
• SMILES: P(=O)(c1ccccc1)(c1ccccc1)C
• Canonical SMILES: CP(=O)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C13H13OP/c1-15(14,12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11H,1H3
• InChIKey: PEGCITODQASXKH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [methyl(phenyl)phosphoroso]benzene
• IUPAC Traditional name: [methyl(phenyl)phosphoroso]benzene
• Synonyms: Diphenylmethylphosphine oxide; Methyldiphenyloxophosphine; NSC 407134; Methyldiphenylphosphine oxide; Methyl(diphenyl)phosphine oxide; 甲基二苯基氧膦; 甲基二苯基氧化膦

Database IDs

• CAS Number: 2129-89-7
• EC Number: 218-346-8
• MDL Number: MFCD00002081
• Beilstein Number: 957291
• PubChem SID: 162070135; 24868914
• PubChem CID: 75041

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.1791
• LogD (pH = 7.4): 3.1791
• Log P: 3.1791
• Molar Refractivity: 63.3716 cm^3
• Polarizability: 25.203615 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 108-110°C; 111-114°C; 111-115 °C(lit.)

Safety Information

• Storage Warning: Harmful/Irritant; Moisture Sensitive
• RTECS: SZ0199480
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38; 22-36/37/38
• Safety Statements: 26-36/37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%; 98+%
• Linear Formula: CH3P(C6H5)2(O)

DETAILS

Sigma Aldrich - 454427

Packaging
5, 25 g in glass bottle
Application
Catalyst for:
• Chlorination and bromination (halogenation) of alcohols under Appel conditions1
• Hydrosilylation reactions2
• Enantioselective cyanosilylation of ketones3
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 454427.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• The lithiated derivative undergoes Horner olefination reactions with carbonyl compounds to give, after dehydration, vinyl or allyl phosphine oxides: Synthesis, 64 (1988). The reaction has been use in a useful synthesis of (3Z,6E)-ɑ-farnesene: J. Org. Chem., 60, 6211 (1995); for reaction scheme see Geranyl bromide, A14093. Epoxides give -hydroxy propylphosphine oxides: J. Chem. Soc., Perkin 1, 2971 (1988); see also: J. Chem. Soc., Perkin 1, 1963 (1999).