Diethyl cyanophosphonate

Base Information

• Chemical Name: Diethyl cyanophosphonate
• CAS No.: 2942-58-7
• Molecular Formula: C5H10NO3P
• Molecular Weight: 163.113
• Hs Code.: 29319090
• European Community (EC) Number: 220-936-5
• UNII: PAD4WPZ7T0
• DSSTox Substance ID: DTXSID90183639
• Nikkaji Number: J50.413K
• Wikidata: Q3008049
• Mol file: 2942-58-7.mol

Synonyms:Ethylphosphorocyanidate (6CI);Phosphonic acid, cyano-, diethyl ester (7CI);Diethoxyphosphoryl cyanide;Diethyl Cyanophosphate;Phosphorocyanidic acid,diethyl ester;Diethyl phosphorocyanidate;Diethylphosphoryl cyanide;

Chemical Property of Diethyl cyanophosphonate

Chemical Property:

• Appearance/Colour: clear colourless to yellow liquid
• Vapor Pressure: 0.158mmHg at 25°C
• Refractive Index: n20/D 1.403(lit.)
• Boiling Point: 214.205 °C at 760 mmHg
• Flash Point: 80.556 °C
• PSA: 69.13000
• Density: 1.154 g/cm³
• LogP: 1.73358
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: DECOMPOSES
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 163.03983018
• Heavy Atom Count: 10
• Complexity: 173

Purity/Quality:

95% ^*data from raw suppliers

Diethyl cyanophosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xi, T+
• Hazard Codes: C,Xi,T+
• Statements: 34-32-26/27/28
• Safety Statements: 26-36-45-50A-36/37/39-28A-36/37-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CCOP(=O)(C#N)OCC
• General Description: Diethyl cyanophosphonate (DCNP) is a highly toxic compound that mimics the nerve agent Tabun, posing significant risks to human health. It is commonly used as a simulant in research due to its structural similarity to lethal nerve agents. DCNP can be detected in water samples using specialized chemosensors, such as carbazole-pyrrole conjugates, which exhibit distinct optical responses upon interaction. Diethyl cyanophosphonate is synthesized through reactions involving dialkyl phosphorochloridates and cyanide sources, yielding high-purity phosphorocyanidates. However, DCNP is relatively unstable and prone to decomposition, particularly in aqueous environments, releasing hazardous hydrogen cyanide. Its applications span peptide chemistry and organic synthesis, though its instability necessitates careful handling.

Technology Process of Diethyl cyanophosphonate

There total 15 articles about Diethyl cyanophosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

hydrogen cyanide (74-90-8) + diethyl chlorophosphate (814-49-3) → diethyl cyanophosphonate (2942-58-7)

Guidance literature:

With triethylamine; In diethyl ether; at 10 - 20 ℃; for 0.25h;

DOI:10.1080/104265090917673

Reference yield: 90.0%

diethyl chlorophosphate (814-49-3) → diethyl cyanophosphonate (2942-58-7)

Guidance literature:

With alkali metal cyanide; at 60 ℃; for 0.0166667h; Microwave irradiation; neat (no solvent);

DOI:10.1080/00397911.2010.517367

Reference yield: 88.0%

sodium cyanide (143-33-9,25596-52-5) + phosphonic acid diethyl ester (762-04-9) → diethyl cyanophosphonate (2942-58-7)

Guidance literature:

With tetrachloromethane; triethylamine; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1055/s-2004-834898

upstream raw materials:

diethyl ether

cyanogen iodide

triethyl phosphite

ethanol

Downstream raw materials:

3-Phenyl-propionic acid 1,1-dicyano-3-phenyl-propyl ester

2-Cyanopyridine

quinoline-2-carbonitrile

2-ethoxyquinoline

Refernces

Chromogenic detection of nerve agent mimics

10.1039/b811247a

The research focuses on the development of a new chromogenic protocol for the selective detection of nerve agent mimics, which are chemical compounds that simulate the behavior of actual nerve agents such as Tabun, Sarin, and Soman. The study addresses the need for quick and reliable detection methods due to the high toxicity and ease of production of these chemicals. The researchers synthesized a chromogenic probe, referred to as chromoreactand 1, using 2-(2-(dimethylamino)phenyl)ethanol (DAPE) as a building block. This probe was designed to undergo a colorimetric change upon interaction with certain organophosphorus (OP) substrates, which are nerve agent simulants. The probe's reactivity was tested with diethyl chlorophosphate (DCP), diisopropyl fluorophosphate (DFP), and diethyl cyanophosphate (DCNP) in acetonitrile. The reaction resulted in a hypsochromic shift, indicating a color change from yellow to colorless due to an intramolecular cyclization process. The detection limit for DCNP and DCP was found to be 1.0 x 10^-4 mol dm^-3. Further experiments involved the preparation of compound 2 to confirm the reaction mechanism through NMR spectroscopy. The probe's reactivity was also studied in mixed water–acetonitrile solutions at pH 7, showing selective bleaching in the presence of DCP, DFP, and DCNP. Kinetic studies were performed to determine the rate constants and half-life of the reaction. The potential application of the probe for in situ sensing was demonstrated by adsorbing it onto silica gel and testing its response to DCP vapor and solution. The study concludes that the developed chromoreactand is a promising alternative for the colorimetric detection of nerve agent simulants, showing selectivity and a rapid response.