diethyl (2-cyanoethyl)phosphonate

• ChemBase ID: 150051
• Molecular Formular: C7H14NO3P
• Molecular Mass: 191.164721
• Monoisotopic Mass: 191.07112994
• SMILES: CCOP(=O)(CCC#N)OCC
• Canonical SMILES: CCOP(=O)(OCC)CCC#N
• InChI: InChI=1S/C7H14NO3P/c1-3-10-12(9,11-4-2)7-5-6-8/h3-5,7H2,1-2H3
• InChIKey: LDOZIDLMPNCNDI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (2-cyanoethyl)phosphonate
• IUPAC Traditional name: diethyl 2-cyanoethylphosphonate
• Synonyms: 3-(Diethylphosphono)propionitrile; NSC 43781; NSC 74863; (2-Cyanoethyl)-phosphonic acid diethyl ester; Diethyl (2-cyanoethyl)phosphonate; (2-氰乙基)-膦酸二乙酯; 二乙基(2-氰乙基)膦酸酯

Database IDs

• CAS Number: 10123-62-3
• EC Number: 233-327-4
• MDL Number: MFCD00013825
• PubChem SID: 24879203; 162244213
• PubChem CID: 82369

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.31306273
• LogD (pH = 7.4): 0.31306273
• Log P: 0.31306273
• Molar Refractivity: 45.5269 cm^3
• Polarizability: 18.22877 Å^3
• Polar Surface Area: 59.32 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 110 °C/0.1 mmHg(lit.)
• Density: 1.08 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4380(lit.)

Safety Information

• RTECS: KI6650000
• 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: 95%
• Linear Formula: NC(CH2)2P(O)(OC2H5)2

DETAILS

Sigma Aldrich - 551163

Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Heteroatom-directed alkyl cyanation of alkynes1
• Use as a fluorescent substrate for carbon-phosphorous lyase2
• Microwave-assisted cleavage of phosphate, phosphonate, and phorphoramide esters3
• Amination and stereoselective olefination for synthesis of HIV-1 antivirals4Reactant for synthesis of:
• Base-catalyzed stereospecific anti-Markovnikov addition reactants5
• Lipophilic oxoamides with activity against phospholipase A26
• Triose phosphate isomerase of muscle inhibitors7