Diethyl cyanophosphonate Property

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

Specific Gravity

1.075

color 

Clear colorless to yellow

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

Hazard Codes 

C,Xi,T+

Risk 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

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

II

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Diethyl cyanophosphonate Chemical Properties,Usage,Production

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.

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.

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.