diethyl [(4-methoxyphenyl)methyl]phosphonate

• ChemBase ID: 90317
• Molecular Formular: C12H19O4P
• Molecular Mass: 258.250621
• Monoisotopic Mass: 258.10209572
• SMILES: O(c1ccc(cc1)CP(=O)(OCC)OCC)C
• Canonical SMILES: CCOP(=O)(Cc1ccc(cc1)OC)OCC
• InChI: InChI=1S/C12H19O4P/c1-4-15-17(13,16-5-2)10-11-6-8-12(14-3)9-7-11/h6-9H,4-5,10H2,1-3H3
• InChIKey: NKARVHNAACNYGE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl [(4-methoxyphenyl)methyl]phosphonate
• IUPAC Traditional name: diethyl (4-methoxyphenyl)methylphosphonate
• Synonyms: [(4-Methoxyphenyl)methyl]phosphonic acid diethyl ester; Diethyl 4-methoxybenzylphosphonate; Diethyl (4-methoxybenzyl)phosphonate; 4-Methoxybenzylphosphonic acid diethyl ester; 4-甲氧基苄基膦酸二乙酯; 4-甲氧基苯基磷酸二乙酯

Database IDs

• CAS Number: 1145-93-3
• EC Number: 214-548-5
• MDL Number: MFCD00015662
• Beilstein Number: 2125148
• PubChem SID: 162077137; 24874531
• PubChem CID: 4063826

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.1436086
• LogD (pH = 7.4): 2.1436086
• Log P: 2.1436086
• Molar Refractivity: 66.8394 cm^3
• Polarizability: 26.73793 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 136-138°C/0.7mm; 136-138°C/0.7mm; 155 °C/0.5 mmHg(lit.)
• Flash Point: >110°C; >110°C(230°F); 110 °C; 230 °F
• Density: 1.5; 1.5 g/mL at 25 °C(lit.); 1.500
• Refractive Index: 1.5045; n20/D 1.504(lit.)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: ≥98%; 98+%
• Linear Formula: CH3OC6H4CH2P(O)(OC2H5)2

DETAILS

Sigma Aldrich - 526088

Packaging
25 g in glass bottle
Application
Reactant for synthesis of:
• γ -Monofluorinated goniothalamin analogs via ring-opening hydrofluorination1
• Stilbenoid derivatives with neuroprotective activity2,3
• Resveratrol-chroman hybrids with antioxidant activity4
• Oligostilbenoids using regioselective cyclodehydration and arylation5
• Resveratrol fatty alcohols with effects on differentiation of neural stem cells and modulation of neuroinflammation6

REFERENCES

• Used in synthesis of C-aryl glycosides: J. Org. Chem., 57, 5670 (1992).