ethyl 2-(dimethoxyphosphoryl)acetate

• ChemBase ID: 74974
• Molecular Formular: C6H13O5P
• Molecular Mass: 196.138181
• Monoisotopic Mass: 196.05006015
• SMILES: P(=O)(OC)(OC)CC(=O)OCC
• Canonical SMILES: CCOC(=O)CP(=O)(OC)OC
• InChI: InChI=1S/C6H13O5P/c1-4-11-6(7)5-12(8,9-2)10-3/h4-5H2,1-3H3
• InChIKey: HUNISAHOCCASGM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(dimethoxyphosphoryl)acetate
• IUPAC Traditional name: ethyl 2-(dimethoxyphosphoryl)acetate
• Synonyms: Ethyl (dimethoxyphosphoryl)acetate; Ethyl (dimethylphosphono)acetate; Dimethyl [(ethoxycarbonyl)methyl]phosphonate 98%; Ethoxycarbonylmethylphosphonic acid dimethylester; Phosphonoacetic acid P,P-dimethyl ethylester; Ethyl dimethylphosphonoacetate; Ethyl 2-(dimethoxyphosphoryl)acetate; 乙氧基羰基甲基膦酸二甲酯; 二甲基膦酰基乙酸乙酯; 乙基膦酰基乙酸二甲酯

Database IDs

• CAS Number: 311-46-6
• EC Number: 206-222-6
• MDL Number: MFCD00015677
• Beilstein Number: 1777603
• PubChem SID: 162039892; 24845338
• PubChem CID: 67555

CALCULATED PROPERTIES

• Acid pKa: 18.266905
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.07297536
• LogD (pH = 7.4): -0.07297536
• Log P: -0.07297536
• Molar Refractivity: 42.1163 cm^3
• Polarizability: 17.420135 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 134 °C/10 mmHg(lit.)
• Flash Point: 210.2 °F; 99 °C
• Density: 1.188 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.435; n20/D 1.435(lit.)

Safety Information

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

Product Information

• Purity: ≥90% (GC); 95+%; 98%
• Grade: technical
• Linear Formula: (CH3O)2P(O)CH2COOC2H5

DETAILS

Sigma Aldrich - 365262

Application
Reactant for synthesis of:
• Non-nucleoside inhibitors of HCV polymerase NS5B1
• Neuropeptide Y1 receptor antagonists2
• Alkenylcarboxylates from Horner-Wadsworth-Emmons reactions3Reactant for:
• Enantioselective transfer hydrogenation for preparation of the C7-C14 fragment of ulapualide A4
• Intramolecular Michael reactions5
• Olefination of peptidyl aldehydes with stabilized ylides6

Sigma Aldrich - 02610

Other Notes
Horner-Wittig reagent7
Application
Reactant for synthesis of:
• Non-nucleoside inhibitors of HCV polymerase NS5B1
• Neuropeptide Y1 receptor antagonists2
• Alkenylcarboxylates from Horner-Wadsworth-Emmons reactions3Reactant for:
• Enantioselective transfer hydrogenation for preparation of the C7-C14 fragment of ulapualide A4
• Intramolecular Michael reactions5
• Olefination of peptidyl aldehydes with stabilized ylides6