diethyl (2-oxo-2-phenylethyl)phosphonate

• ChemBase ID: 74939
• Molecular Formular: C12H17O4P
• Molecular Mass: 256.234741
• Monoisotopic Mass: 256.08644565
• SMILES: P(=O)(OCC)(OCC)CC(=O)c1ccccc1
• Canonical SMILES: CCOP(=O)(CC(=O)c1ccccc1)OCC
• InChI: InChI=1S/C12H17O4P/c1-3-15-17(14,16-4-2)10-12(13)11-8-6-5-7-9-11/h5-9H,3-4,10H2,1-2H3
• InChIKey: HPEVTTNSIPGLEL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (2-oxo-2-phenylethyl)phosphonate
• IUPAC Traditional name: diethyl 2-oxo-2-phenylethylphosphonate
• Synonyms: 2-(Diethoxyphosphoryl)acetophenone; Diethyl (2-oxo-2-phenylethyl)phosphonate; Diethyl benzoylmethylphosphonate; Diethyl phenacylphosphonate; NSC 648426; Diethyl (2-oxo-2-phenylethyl)phosphonate; (2-氧代-2-苯乙基)膦酸二乙酯

Database IDs

• CAS Number: 3453-00-7
• MDL Number: MFCD00015342
• PubChem SID: 24865704; 162039857
• PubChem CID: 372803

CALCULATED PROPERTIES

• Acid pKa: 15.866785
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.8223808
• LogD (pH = 7.4): 1.8223808
• Log P: 1.8223808
• Molar Refractivity: 65.9129 cm^3
• Polarizability: 26.124123 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 148-150°C/0.5mm; 192-193 °C/11 mmHg(lit.)
• Flash Point: >113 °C; >113°C; >235.4 °F
• Density: 1.179; 1.179 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.513(lit.)

Safety Information

• Storage Warning: Harmful/Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: 97%
• Linear Formula: C6H5COCH2P(O)(OC2H5)2

DETAILS

Sigma Aldrich - 410756

Packaging
1, 10 g in glass bottle
Application
Reactant involved in:
• Asymmetric Michael addition of β-oxo phosphonates to nitro olefins1
• Gem-chlorofluorination of keto phosphonates with subsequent functionalization of the products2
• Cyclocondensation reactions to produce arylphosphonates3
• Diazo transfer reactions for synthesis of diazo-phosphonyl compounds4
• Horner-Wadsworth-Emmons reactions5
• Inverse-electron-demand Diels-Alder reactions6