prop-2-en-1-yl 2-(diethoxyphosphoryl)acetate

• ChemBase ID: 140654
• Molecular Formular: C9H17O5P
• Molecular Mass: 236.202041
• Monoisotopic Mass: 236.08136027
• SMILES: CCOP(=O)(CC(=O)OCC=C)OCC
• Canonical SMILES: CCOP(=O)(CC(=O)OCC=C)OCC
• InChI: InChI=1S/C9H17O5P/c1-4-7-12-9(10)8-15(11,13-5-2)14-6-3/h4H,1,5-8H2,2-3H3
• InChIKey: USZLAMOPIWNLPH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-en-1-yl 2-(diethoxyphosphoryl)acetate
• IUPAC Traditional name: prop-2-en-1-yl 2-(diethoxyphosphoryl)acetate
• Synonyms: Phosphonoacetic acid P,P-diethyl allyl ester; Allyl P,P-diethylphosphonoacetate; 膦酰基乙酸P,P-二乙基烯丙酯; P,P-二乙基膦酰基乙酸烯丙酯

Database IDs

• CAS Number: 113187-28-3
• MDL Number: MFCD00191710
• Beilstein Number: 1788582
• PubChem SID: 162234895; 24865325
• PubChem CID: 4583084

CALCULATED PROPERTIES

• Acid pKa: 18.17784
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.0076565
• LogD (pH = 7.4): 1.0076565
• Log P: 1.0076565
• Molar Refractivity: 56.0276 cm^3
• Polarizability: 22.61109 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 157-158 °C/10 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Density: 1.12 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.445(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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)CH2COOCH2CH=CH2

DETAILS

Sigma Aldrich - 405701

Packaging
5, 25 mL in glass bottle
Application
Reactant for:
• Horner-Wadsworth-Emmons reaction1
• Preparation of phosphonate-functionalized cyclopentenones via regioselective Pauson-Khand processes2
• Preparation of salicylihalamide analog saliphenylhalamide as potential vacuolar ATPase inhibitors and anticancer agents3
• Solid-phase synthesis of olefin-containing peptides via Horner-Emmons reaction as inhibitors of HTLV-1 protease4
• Synthesis of fluorescent poly(aromatic amide) dendrimers5