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
• Uses: Diethyl cyanophosphonate was used in the synthesis of 4-acylthiol-4-deoxy-4′-demethyl epipodophyllotoxin analogs. Coupling reagent for peptide synthesis. Reagent for the phosphorylation of phenols. Activating agent for fluorescent derivatization of carboxylic acids which allows separation by HPLC.

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:

2,4,6-Trimethoxybenzoyldiaethylphosphat

2-Cyanopyridine

quinoline-2-carbonitrile

2-ethoxyquinoline

Refernces

• 1、 Shi, Enxue,Pei, Chengxin. "Synthesis of phosphorocyanidates via phosphorochloridates". . p. 1093 - 1099. Retrieved 2003.
• 2、 Sun, Daoming,Shi, Enxue,Xiao, Junhua,Pei, Chengxin. "An efficient synthesis of dialkyl phosphorocyanidates". . p. 2155 - 2161. Retrieved 2005.
• 3、 Shi, Enxue,Xiao, Junhua,Pei, Chengxin,Chen, Jisheng. "Microwave-assisted solvent-free synthesis of pseudohalophosphates". experimental part. p. 3085 - 3088. Retrieved 2011/09/12.
• 4、 Shi, Enxue,Pei, Chengxin. "Phase-transfer catalyzed pseudohalogenation of phosphorochloridates". . p. 669 - 673. Retrieved 2007/10/03.