diethyl (2-phenylethyl)phosphonate

• ChemBase ID: 149797
• Molecular Formular: C12H19O3P
• Molecular Mass: 242.251221
• Monoisotopic Mass: 242.1071811
• SMILES: CCOP(=O)(CCc1ccccc1)OCC
• Canonical SMILES: CCOP(=O)(CCc1ccccc1)OCC
• InChI: InChI=1S/C12H19O3P/c1-3-14-16(13,15-4-2)11-10-12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3
• InChIKey: WEXGRJPJMNUCMG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (2-phenylethyl)phosphonate
• IUPAC Traditional name: diethyl 2-phenylethylphosphonate
• Synonyms: Diethyl 2-phenylethyl phosphonate; 2-苯乙基膦酸二乙酯

Database IDs

• CAS Number: 54553-21-8
• MDL Number: MFCD03093992
• PubChem SID: 24878557; 162243959
• PubChem CID: 3448525

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.6139925
• LogD (pH = 7.4): 2.6139925
• Log P: 2.6139925
• Molar Refractivity: 65.1312 cm^3
• Polarizability: 26.042128 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 125 °C/0.25 mmHg(lit.)
• Flash Point: >110 °C; >230 °F
• Density: 1.054 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.495(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: 98%
• Linear Formula: C6H5(CH2)2PO(OC2H5)2

DETAILS

Sigma Aldrich - 541788

Packaging
10 g in glass bottle
Application
Reactant for:
• Preparation of 1,3-diketones, β-keto esters, and β-keto phosphonates via 1,2-addition of carbanionic nucleophiles to cyclic vinylogous acyl triflates, followed by ring-opening fragmentation, Claisen condensation and carbon-carbon bond cleavage1
• Controlling the surface state emission in ultrasmall CdSe nanocrystals2
• Reactions with organoboranes for synthesis of organophosphorous compounds3