| Identification | More | [Name]
Diethyl cyanophosphonate | [CAS]
2942-58-7 | [Synonyms]
CYANOPHOSPHONIC ACID DIETHYL ESTER
DEPC
DIETHYL CYANOPHOSPHATE
DIETHYL CYANOPHOSPHONATE
DIETHYL PHOSPHOROCYANIDATE
DIETHYLPHOSPHORYL CYANIDE
(ETO)2P(O)CN
Diethoxy-phosphoryl cyanide
diethoxy-phosphorylcyanide
Diethyl cyanidophosphate
Diethyl cyanophosphosphonate
diethylcyanophosphosphonate
Phosphorocyanidic acid, diethyl ester
Phosphorocyanidic acid, O,O-diethyl ester
phosphorocyanidicacid,o,o-diethylester
DEPC DIETHYLCYANOPHOSPHONATE
DEPC (Diethyl phosphoryl cyanide)
Diethypyrocarbonate
DIETHYL CYANOPHOSPHONATE: TECH., 90%
DEPC | [EINECS(EC#)]
220-936-5 | [Molecular Formula]
C5H10NO3P | [MDL Number]
MFCD00010256 | [Molecular Weight]
163.11 | [MOL File]
2942-58-7.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colourless to yellow liquid | [Boiling point ]
104-105 °C19 mm Hg(lit.) | [density ]
1.075 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.403(lit.)
| [Fp ]
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 Data | Back Directory | [Hazard Codes ]
C,Xi,T+ | [Risk Statements ]
R34:Causes burns.
R32:Contact with acids liberates very toxic gas.
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [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 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Cyanogen bromide-->DIETHYL PHOSPHATE-->TEPP-->Phosphorocyanidous acid diethyl ester-->CYANOGEN IODIDE-->CHLOROCARBONYLSULFENYL CHLORIDE-->POTASSIUM CYANIDE-->Diethyl chlorophosphate | [Preparation Products]
Foscarnet sodium-->1H-[1]-BENZAZEPHE-2,5(3H, 4H)-DIONE-->tert-butyl (5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oate-->4-Cyanotetrahydro-4H-pyran-->Pazinaclone-->1-METHYL-3-PHENYLPROPYLISOCYANIDE |
| Hazard Information | Back Directory | [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.
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