diethyl (1-cyanoethyl)phosphonate

• ChemBase ID: 145281
• Molecular Formular: C7H14NO3P
• Molecular Mass: 191.164721
• Monoisotopic Mass: 191.07112994
• SMILES: CCOP(=O)(C(C)C#N)OCC
• Canonical SMILES: CCOP(=O)(C(C#N)C)OCC
• InChI: InChI=1S/C7H14NO3P/c1-4-10-12(9,11-5-2)7(3)6-8/h7H,4-5H2,1-3H3
• InChIKey: UMLWEPGSWQNXQX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (1-cyanoethyl)phosphonate
• IUPAC Traditional name: diethyl 1-cyanoethylphosphonate
• Synonyms: (1-Cyanoethyl)phosphonic acid diethyl ester; NSC 135193; Diethyl (1-cyanoethyl)phosphonate; DIETHYL (1-CYANOETHYL)PHOSPHONATE; 二乙基(1-氰乙基)膦酸酯

Database IDs

• CAS Number: 29668-61-9
• MDL Number: MFCD01457302
• PubChem SID: 24865577; 162239489
• PubChem CID: 282103

CALCULATED PROPERTIES

• Acid pKa: 12.32482
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.6996716
• LogD (pH = 7.4): 0.6996665
• Log P: 0.6996717
• Molar Refractivity: 45.569 cm^3
• Polarizability: 18.22877 Å^3
• Polar Surface Area: 59.32 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 140-141 °C/11 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.085 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.432(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%; 98%
• Linear Formula: CH3CH(CN)P(O)(OC2H5)2

DETAILS

Sigma Aldrich - 408573

Packaging
5 g in glass bottle
Application
Reacant for:
• Preparation of sphingosine phosphate receptor (S1P) agonists with N-cinnamyl-β-alanine moiety1
• Preparation of benzyl- and benzoyldimethylaminopyridinones as HIV-1 reverse transcriptase inhibitors2
• Stereoselective preparation of cyano(trifluoromethyl)pentenenitriles via alkylation, followed by elimination reaction3
• Synthesis of [(methylenepiperidinyl) or (methylenepyrrolidinyl)fluorophenyl]oxazolidinone antibacterial agents4
• Horner-Wadsworth-Emmons olefination5