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| | Diethyl cyanophosphonate Basic information |
| | Diethyl cyanophosphonate Chemical Properties |
| 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 | | InChI | 1S/C5H10NO3P/c1-3-8-10(7,5-6)9-4-2/h3-4H2,1-2H3 | | InChIKey | ZWWWLCMDTZFSOO-UHFFFAOYSA-N | | SMILES | CCOP(=O)(OCC)C#N | | CAS DataBase Reference | 2942-58-7(CAS DataBase Reference) | | NIST Chemistry Reference | Diethyl cyanophosphonate(2942-58-7) |
| 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 | | Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | | Hazard Classifications | Acute Tox. 2 Dermal
Acute Tox. 2 Inhalation
Acute Tox. 2 Oral
Eye Dam. 1
Skin Corr. 1B |
| | Diethyl cyanophosphonate Usage And Synthesis |
| 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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| | Diethyl cyanophosphonate Preparation Products And Raw materials |
| 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 |
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