ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate

• ChemBase ID: 7246
• Molecular Formular: C8H16FO5P
• Molecular Mass: 242.1818042
• Monoisotopic Mass: 242.07193846
• SMILES: O=C(C(P(=O)(OCC)OCC)F)OCC
• Canonical SMILES: CCOC(=O)C(P(=O)(OCC)OCC)F
• InChI: InChI=1S/C8H16FO5P/c1-4-12-8(10)7(9)15(11,13-5-2)14-6-3/h7H,4-6H2,1-3H3
• InChIKey: FVPISMANESAJQZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate
• IUPAC Traditional name: ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate
• Synonyms: Triethyl 2-fluoro-2-phosphonoacetate; 2-Fluoro-2-phosphonoacetic acid triethyl ester; Ethyl (diethoxyphosphonyl)(fluoro)acetate; 2-Fluoro-2-phosphonoacetic acid triethyl ester; Diethyl [(ethoxycarbonyl)fluoromethyl]phosphonate 96%; Diethyl [(ethoxycarbonyl)fluoromethyl]phosphonate; Ethyl diethylphosphonofluoroacetate; Triethyl 2-fluoro-2-phosphonoacetate; ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate; 2-氟代膦-2-酰乙酸三乙脂; 2-氟-2-膦酰基乙酸三乙酯

Database IDs

• CAS Number: 2356-16-3
• MDL Number: MFCD00134400
• Beilstein Number: 1912161
• PubChem SID: 24863330; 160970553
• PubChem CID: 2734865

CALCULATED PROPERTIES

• Acid pKa: 16.44774
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.1975211
• LogD (pH = 7.4): 1.1975211
• Log P: 1.1975211
• Molar Refractivity: 51.1198 cm^3
• Polarizability: 20.897814 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 75 °C/0.01 mmHg(lit.); 75°C/0.01mm; 75°C/0.01mm
• Flash Point: 163.4 °F; 73 °C; 73°C(163°F)
• Density: 1.194; 1.194 g/mL at 25 °C(lit.)
• Refractive Index: 1.425; 1.4250; n20/D 1.425(lit.); n20/D 1.625
• Hydrophobicity(logP): 1.205

Safety Information

• Storage Warning: Irritant; IRRITANT, FLAMMABLE
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥96% (GC); 95%; 96%; 97%
• Grade: technical
• Linear Formula: (C2H5O)2P(O)CH(F)CO2C2H5

DETAILS

Apollo Scientific Ltd - PC4179D

Fluorinated Horner's reagent

Sigma Aldrich - 374717

Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Diels-Alder reactions1
• Biosynthesis of terpene2
• Stereoselective synthesis of unsaturated esters, fluorides and nitriles from the reactions of aldehydes and ketones using Wadsworth-Emmons phosphonates3
• Synthesis of quinolones4
• Horner-Wadsworth-Emmons asymmetric hydration5
• Addition reactions and the subsequent application to click chemistry6
• Asymmetric intermolecular Stetter reactions7

Sigma Aldrich - 47400

Other Notes
Horner-Wittig reagent for the synthesis of α-fluoro-α,β-unsaturated esters8,9,10
Application
Reactant for:
• Diels-Alder reactions1
• Biosynthesis of terpene2
• Stereoselective synthesis of unsaturated esters, fluorides and nitriles from the reactions of aldehydes and ketones using Wadsworth-Emmons phosphonates3
• Synthesis of quinolones4
• Horner-Wadsworth-Emmons asymmetric hydration5
• Addition reactions and the subsequent application to click chemistry6
• Asymmetric intermolecular Stetter reactions7