2942-58-7

Basic information

• Product Name: Diethyl cyanophosphonate
• Synonyms: DIETHYL PHOSPHOROCYANIDATE;DIETHYLPHOSPHORYL CYANIDE;DIETHYL CYANOPHOSPHATE;DIETHYL CYANOPHOSPHONATE;CYANOPHOSPHONIC ACID DIETHYL ESTER;(ETO)2P(O)CN;Diethoxy-phosphoryl cyanide;diethoxy-phosphorylcyanide
• CAS NO: 2942-58-7
• Molecular Formula: C₅H₁₀NO₃P
• Molecular Weight: 163.11
• EINECS: 220-936-5
• Product Categories: Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Synthetic Organic Chemistry
• Mol File: 2942-58-7.mol

Chemical Properties

• Boiling Point: 104-105 °C19 mm Hg(lit.)
• Flash Point: 177 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.075 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.158mmHg at 25°C
• Refractive Index: n20/D 1.403(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: DECOMPOSES
• Sensitive: Moisture Sensitive
• BRN: 1768938
• CAS DataBase Reference: Diethyl cyanophosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl cyanophosphonate(2942-58-7)
• EPA Substance Registry System: Diethyl cyanophosphonate(2942-58-7)

Safety Data

• Hazard Codes: C,Xi,T+
• Statements: 34-32-26/27/28
• Safety Statements: 26-36-45-50A-36/37/39-28A-36/37-28
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• RTECS: TD2500000
• F: 10-13-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2942-58-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Diethyl cyanophosphonate is used as a reagent for the synthesis of 4-acylthiol-4-deoxy-4′-demethyl epipodophyllotoxin analogs, which are important compounds in the development of pharmaceuticals.
Used in Peptide Synthesis:
DCNP serves as a coupling reagent in peptide synthesis, facilitating the formation of peptide bonds between amino acid residues.
Used in Phosphorylation of Phenols:
Diethyl cyanophosphonate is utilized as a reagent for the phosphorylation of phenols, a crucial process in various chemical reactions and applications.
Used in Fluorescent Derivatization:
DCNP acts as an activating agent for the fluorescent derivatization of carboxylic acids, enabling their separation by high-performance liquid chromatography (HPLC), which is essential for analytical and preparative purposes in various industries.
Used in Detection of Nerve Agents:
Diethyl cyanophosphonate is used in the detection of nerve agents through its interaction with fluorescein, a reversible fluorescent sensor, which aids in the identification and monitoring of these hazardous substances.
Used in Environmental and Safety Research:
The degradation of DCNP in the presence of suitable organocatalysts, such as different amines, aminoalcohols, and glycols, has been studied to understand its behavior in the environment and to develop methods for safe handling and disposal.

InChI:InChI=1/C5H10NO3P/c1-3-8-10(7,5-6)9-4-2/h3-4H2,1-2H3

Upstream product

• 60-29-7 diethyl ether 
• 506-78-5 cyanogen iodide 
• 122-52-1 triethyl phosphite 
• 64-17-5 ethanol 
• 35156-51-5 Dichlorisocyanatomethyl-phosphonsaeuredichlorid 
• 506-68-3 bromocyane 
• 33326-12-4 diethyl phosphorocyanidite 
• 7677-24-9 trimethylsilyl cyanide 
• 814-49-3 diethyl chlorophosphate 
• 143-33-9 sodium cyanide 
• 107-49-3 Tetraethyl pyrophosphate 
• 151-50-8 potassium cyanide 
• 2757-23-5 chloro(chlorosulfanyl)methanone 
• 163678-89-5 O,O-diethyl(thiocarbamoyl)phosphonate 

Downstream Products

• 29936-58-1 2,4,6-Trimethoxybenzoyldiaethylphosphat 
• 5467-94-7 α-Benzoyloxy-α-phenylmalononitrile 
• 63064-21-1 3-Phenyl-propionic acid 1,1-dicyano-3-phenyl-propyl ester 
• 100-70-9 2-Cyanopyridine 
• 115464-35-2 2-(1,2-diaminoethyl)pyridine 
• 111571-84-7 phosphoric acid 1-cyano-3-phenylallyl ester diethyl ester 
• 855476-42-5 phosphoric acid 1-cyano-3-phenylpropyl ester diethyl ester 
• 1436-43-7 quinoline-2-carbonitrile 
• 46185-83-5 2-ethoxyquinoline 
• 1198-30-7 1-isoquinolinecarbonitrile 
• 78-40-0 triethyl phosphate 
• 26218-72-4 3,4-bis-(4-chloro-phenyl)-furazan 2-oxide 
• 87174-54-7 [3-(4-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-phosphonic acid diethyl ester 
• 112163-39-0 7-cyanomethotrexate dimethyl ester 

Relevant articles and documents

A unique dual sensor for the detection of DCNP (nerve agent mimic) and Cd2+ in water

Both DCNP (nerve gas Tabun mimic) and Cd2+ are extremely toxic to mankind. We have focused our research on quantitative estimation of DCNP and Cd2+ in given water samples. A carbazole-pyrrole conjugate CPC has been designed and synthesized which possesses a unique characteristic feature of detecting two hazardous analytes DCNP and Cd2+ by giving two different optical responses i.e. visual color changes and fluorescence "turn-on" respectively. The PET based chemosensor CPC produces a new compound CPC-1 and a highly fluorescent CPC-Cd2+ complex upon addition of DCNP and Cd2+, respectively. The detection limit of CPC for DCNP and Cd2+ has been estimated to be 7.75 nM and 0.27 μM, respectively, at pH 7.0. Quantum chemical calculations have been executed to demonstrate the electronic properties and the mechanism of the receptor-donor interactions. The concentrations of DCNP and Cd2+ ions in various water samples have been estimated with the help of standard absorbance and fluorescence curves.

Synthesis of phosphorocyanidates via phosphorochloridates

Dialkyl phosphorocyanidates (2) were obtained from dialkyl phosphorochloridates (1) in high yield (80-86%) at room temperature in methyl cyanide. Reaction between diethyl phosphorochloridate and potassium cyanide was greatly influenced by the solvents use

A Novel Phase Transfer Catalyzed Synthesis of Dialkyl Phosphorocyanidates from Dialkyl Phosphorochloridates

Dialkyl phosphorocyanidates 2a-2d were prepared from dialkyl phosphorochloridates 1a-1d and potassium cyanide in high yield under phase transfer catalyzed conditions.

An efficient synthesis of dialkyl phosphorocyanidates

Dialkyl phosphorocyanidates 2a-2g were prepared in high yield from dialkyl phosphorochloridates and hydrogen cyanide in the presence of triethylamine in ether. The white precipitates formed in the reaction of diethyl phosphorochlorodates and triethylamine were verified as triethylammonium chloride, not the similar phosphoryltriethylammonium chloride by FAB-MS, ESI-MS, 31P-NMR, and 1H-NMR. Copyright Taylor & Francis Inc.

New route to O,O-diethyl phosphorocyanidate

A new and efficient route for synthesis of O, O-Diethyl Phosphorocyanidate by decomposition of diethyl phosphoryl-1,2,4,-dithiazolin-5-one was discussed. The use of phosphorocyanidates as coupling reagents in peptide chemistry and other applications of these compounds in organic synthesis was also demonstrated. It was found that these compounds were relatively unstable and could decompose easily, especially in the presence of water with the formation of hydrogen cyanide. A new efficient route to O, O-dialkyl phosphorocyamidates was offered, which were not contaminated by isomeric isocyanidates and could be used as the substrates for further synthetic purposes.

Microwave-assisted solvent-free synthesis of pseudohalophosphates

A rapid, efficient, solvent-free, and catalyst-free procedure has been developed for the synthesis of pseudohalophosphates from phosphorochloridate and sodium (or potassium) pseudohalides under microwave irradiation. Diethyl, diisobutyl, and diphenyl phosphorazidates, phosphorocyanidates, and phosphor(isothiocyanidate)s 2a-2i were prepared in good yields under mild conditions. Copyright

Radical cyanation of alkyl iodides with diethylphosphoryl cyanide

The β-elimination of an organophosphoryl group from an iminyl radical is observed for the first time. On the basis of this finding, radical cyanation of alkyl iodides is achieved by using diethylphosphoryl cyanide. Georg Thieme Verlag Stuttgart.

Phase-transfer catalyzed pseudohalogenation of phosphorochloridates

Pseudohalogenation of phosphorochloridates by sodium pseudohalides with different phase transfer catalysts and solvents was optimized. Dialkyl and diaryl phosphorazidates phosphorocyanidates, and phosphor(isotniocyanidate)s were prepared in good yields from phosphorochloridates under two kinds of mild phase-transfer catalyzed conditions respectively.

Pseudohalogenation of phosphites

A new type of Atherton-Todd reaction for a convenient pseudohalogenation of phosphites has been developed. Direct azidation, cyanation, and thiocyanation of (RO)2P(O)H (R = Et, i-Bu, Ph) were accomplished readily with sodium pseudohalides in acetonitrile under mild modified Atherton-Todd conditions. The corresponding phosphorochloridates were demonstrated by GC/MS to be the intermediates. Pseudohalogenations of ethyl phenylphosphinate and diphenylphosphine oxide were also investigated.

Method for preparing cyanophosphonate derivatives from phosphate esters and cyanide

A process for preparing cyanophosphonate derivatives involves contacting a phosphate ester and cyanide in a reaction mixture under conditions sufficient to produce a cyanophosphonate derivative. That cyanophosphonate derivative product can subsequently be hydrogenated to produce an aminomethylphosphonate derivative.