ethyl 2-(diethoxyphosphoryl)propanoate

• ChemBase ID: 91243
• Molecular Formular: C9H19O5P
• Molecular Mass: 238.217921
• Monoisotopic Mass: 238.09701034
• SMILES: P(=O)(OCC)(OCC)C(C)C(=O)OCC
• Canonical SMILES: CCOC(=O)C(P(=O)(OCC)OCC)C
• InChI: InChI=1S/C9H19O5P/c1-5-12-9(10)8(4)15(11,13-6-2)14-7-3/h8H,5-7H2,1-4H3
• InChIKey: BVSRWCMAJISCTD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(diethoxyphosphoryl)propanoate
• IUPAC Traditional name: ethyl 2-(diethoxyphosphoryl)propanoate
• Synonyms: Triethyl 2-phosphonopropionate; Ethyl 2-(diethoxyphosphoryl)propanoate; Diethyl [1-(ethoxycarbonyl)ethyl]phosphonate 97%; ethyl 2-(diethoxyphosphoryl)propanoate; Diethyl ethoxycarbonylethyl-phosphonate; TRIETHYL 2-PHOSPHONOPROPIONATE; 2-(Diethoxyphosphoryl)propionic acid ethyl ester; Triethyl 2-phosphonopropionate; Diethyl 1-(ethoxycarbonyl)ethanephosphonate; 2-Phosphonopropionic acid triethyl ester; 2-膦酰丙酸三乙酯; 2-膦酰丙酸三乙脂

Database IDs

• CAS Number: 3699-66-9
• EC Number: 223-033-4
• MDL Number: MFCD00009159
• Beilstein Number: 1786994
• PubChem SID: 24850353; 162077947
• PubChem CID: 107155

CALCULATED PROPERTIES

• Acid pKa: 18.457832
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.1510886
• LogD (pH = 7.4): 1.1510886
• Log P: 1.1510886
• Molar Refractivity: 56.1074 cm^3
• Polarizability: 22.862322 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 102-104°C; 143-144 °C/12 mmHg(lit.); 143-144°C/12mm
• Flash Point: 192.2 °F; 88°C; 88°C(190°F); 89 °C
• Density: 1.111; 1.111 g/mL at 25 °C(lit.)
• Refractive Index: 1.431; 1.4320; n20/D 1.431(lit.)
• Hydrophobicity(logP): 1.161

Safety Information

• Storage Condition: 0°C
• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• TSCA Listed: 否
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 95%; 98%
• Linear Formula: (C2H5O)2P(O)CH(CH3)CO2C2H5

DETAILS

MP Biomedicals - 02157017

(Diethyl ethoxycarbonylethyl-phosphonate)

Sigma Aldrich - 174653

Packaging
10, 50 g in glass bottle
Application
Reactant involved in:
• Intramolecular conjugate addition for the synthesis of floresolide B1
• Chemoenzymatic one-pot synthesis of γ-butyrolactones2
• Enantioselective synthesis of spiroindane di-Me acetic acid via asymmetric hydrogenation3
• Stereoselective intramolecular Diels-Alder reactions4,5
• Horner-Wadsworth-Emmons reactions6
This Wittig-Horner reagent condenses with a wide variety of aldehydes and ketones to form acrylates.

REFERENCES

• Wadsworth-Emmons precursor of methacrylic esters (see Triethyl phosphonoacetate, A14120 and Appendix 1). Lithiation followed by acylation with perfluoroalkanoic anhydrides gives a perfluoroacyl intermediate which, with an organolithium reagent, leads stereoselectively to a trifluoroalkylated ɑ?-unsaturated ester: J. Fluorine Chem., 89, 141 (1998):