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HomeProduct name listDiethyl cyanophosphonate

Diethyl cyanophosphonate

Synonym(s):DEPC;Diethyl phosphoryl cyanide

  • CAS NO.:2942-58-7
  • Empirical Formula: C5H10NO3P
  • Molecular Weight: 163.11
  • MDL number: MFCD00010256
  • EINECS: 220-936-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-07-11 17:04:31
Diethyl cyanophosphonate Structural

What is Diethyl cyanophosphonate?

Chemical properties

Diethyl cyanophosphonate is a clear colourless to yellow liquid. It soluble in most common organic solvents , such as dimethylformamide , tetrahydrofuran , diethyl ether , and toluene. Diethyl cyanophosphonate is highly toxic and corrosive. lt must be handled in awell-ventilated fume hood. In addition, it is moisture sensitive and should bestored in a refrigerator under nitrogen.

The Uses of Diethyl cyanophosphonate

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.

What are the applications of Application

1973 Harusawa et al. found that diethyl phosphorocyanidate (diethyl cyanophosphonate; depc), a cyano and diethyl analog of DPPA, was a valuable reagent for peptide synthesis. DEPC is a practical and versatile reagent for organic synthesis, particularly as a condensing reagent for the synthesis of amides and peptides and its application in O-, S-, and C-acylations. Compared to other cyanating agents, DEPC is significantly less toxic and commercially available. DEPC can also be employed as a cyanating agent for introducing a C1 unit into a range of compounds, and its reaction with carbonyl compounds in the presence of a catalyst easily affords CPs, which are key intermediates in a variety of reactions[1].

General Description

Diethyl cyanophosphonate (DCNP, a Tabun mimic, DECP) is a nerve agent simulant. Its detection by using fluorescein, a reversible fluorescent sensor, has been reported. Its degradation in the presence of suitable organocatalysts (different amines, aminoalcohols and glycols) has been studied.

References

[1] Shinya Harusawa , Takayuki Shioiri. “Diethyl phosphorocyanidate (DEPC): a versatile reagent for organic synthesis.” Tetrahedron 72 50 (2016): Pages 8125-8200.

Properties of Diethyl cyanophosphonate

Boiling point: 104-105 °C19 mm Hg(lit.)
Density  1.075 g/mL at 25 °C(lit.)
refractive index  n20/D 1.403(lit.)
Flash point: 177 °F
storage temp.  2-8°C
solubility  Acetonitrile (Slightly), Chloroform (Slightly)
form  Liquid
color  Clear colorless to yellow
Specific Gravity 1.075
Water Solubility  DECOMPOSES
Sensitive  Moisture Sensitive
BRN  1768938
Exposure limits NIOSH: IDLH 25 mg/m3
Stability: Moisture Sensitive
CAS DataBase Reference 2942-58-7(CAS DataBase Reference)
NIST Chemistry Reference Diethyl cyanophosphonate(2942-58-7)

Safety information for Diethyl cyanophosphonate

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H314:Skin corrosion/irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Diethyl cyanophosphonate

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