ethyl 2-chloro-2-(diethoxyphosphoryl)acetate

• ChemBase ID: 148292
• Molecular Formular: C8H16ClO5P
• Molecular Mass: 258.636401
• Monoisotopic Mass: 258.04238792
• SMILES: CCOC(=O)C(P(=O)(OCC)OCC)Cl
• Canonical SMILES: CCOC(=O)C(P(=O)(OCC)OCC)Cl
• InChI: InChI=1S/C8H16ClO5P/c1-4-12-8(10)7(9)15(11,13-5-2)14-6-3/h7H,4-6H2,1-3H3
• InChIKey: PCDXCIMROXIFBI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-chloro-2-(diethoxyphosphoryl)acetate
• IUPAC Traditional name: ethyl 2-chloro-2-(diethoxyphosphoryl)acetate
• Synonyms: Chloro(diethoxyphosphinyl)acetic acid ethyl ester; Triethyl 2-chloro-2-phosphonoacetate; 2-氯-2-膦酰基乙酸三乙酯

Database IDs

• CAS Number: 7071-12-7
• MDL Number: MFCD00192516
• PubChem SID: 24864786; 162242468
• PubChem CID: 3604459

CALCULATED PROPERTIES

• Acid pKa: 15.550629
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.7004231
• LogD (pH = 7.4): 1.7004231
• Log P: 1.7004231
• Molar Refractivity: 55.8629 cm^3
• Polarizability: 22.972359 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 93-95 °C/0.01 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.21 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.446(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: 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: 97%
• Linear Formula: (C2H5O)2P(O)CH(Cl)CO2C2H5

DETAILS

Sigma Aldrich - 399086

Packaging
5 mL in glass bottle
Application
Reactant involved in:
• Synthesis of purine nucleoside derivatives containing a halogen atom1
• Horner-Wadsworth-Emmons reactions2,3
• Scale-up production of bacterial topoisomerase inhibitors4
• Synthesis of galbonolide derivatives5
• Stereoselective Horner reaction for preparation of vinylogous peptides6