diethyl cyanophosphonate

• ChemBase ID: 87627
• Molecular Formular: C5H10NO3P
• Molecular Mass: 163.111561
• Monoisotopic Mass: 163.03982982
• SMILES: P(=O)(C#N)(OCC)OCC
• Canonical SMILES: CCOP(=O)(C#N)OCC
• InChI: InChI=1S/C5H10NO3P/c1-3-8-10(7,5-6)9-4-2/h3-4H2,1-2H3
• InChIKey: ZWWWLCMDTZFSOO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl cyanophosphonate
• IUPAC Traditional name: diethylphosphorocyanidate
• Synonyms: Diethyl phosphorocyanidate; (Diethoxyphosphoryl)cyanide; Diethyl cyanophosphonate; Diethyl cyanophosphonate; diethyl phosphorocyanidate; DEPC; Diethyl phosphoryl cyanide; 氰代磷酸二乙酯; 氰基膦酸二乙酯

Database IDs

• CAS Number: 2942-58-7
• EC Number: 220-936-5
• MDL Number: MFCD00010256
• Beilstein Number: 1768938
• PubChem SID: 162074667; 24870809; 24857217
• PubChem CID: 76257

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.63806987
• LogD (pH = 7.4): 0.63806987
• Log P: 0.63806987
• Molar Refractivity: 36.9701 cm^3
• Polarizability: 14.597984 Å^3
• Polar Surface Area: 59.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 104-105 °C/19 mmHg(lit.); 104-105°C; 104-105°C/19mm; 104-105°C/19mm
• Flash Point: 176 °F; 80 °C; 80°C; 80°C(176°F)
• Density: 1.075; 1.075 g/mL at 25 °C(lit.); 1.091 g/ml
• Refractive Index: 1.4010; n20/D 1.403(lit.)

Safety Information

• Storage Condition: 2-8°C, Store Under Nitrogen
• Storage Warning: Corrosive/Very Toxic/Stench/Moisture Sensitive/Store under Argon/Keep Cold; Moisture Sensitive
• RTECS: TD2500000
• European Hazard Symbols: Corrosive (C); Highly toxic (T+); Harmful (Xn)
• UN Number: 2922; UN2922
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 26/27/28-32-34; 26/27/28-34; R:22-34
• Safety Statements: 26-28-36/37/39-45; 26-28-36/37-45; S:16-26-27/28-36/37/39-46
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300 +H310 + H330-H314; H300-H310-H330-H314-H318-H227
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350; P280-P305+P351+P338-P302+P352-P304+P340-P309-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 2
• Supplemental Hazard Statements: Contact with acids liberates very toxic gas.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (GC); 90%; tech. 90%
• Grade: technical
• Linear Formula: (CH3CH2O)2P(O)CN

DETAILS

MP Biomedicals - 02150888

Coupling reagent for peptide synthesis.

Sigma Aldrich - 472565

Other Notes
Contains triethyl phosphate
Packaging
5, 25, 100 mL in glass bottle
Application
Coupling reagent for peptide synthesis.1 Reagent for the phosphorylation of phenols.2 Activating agent for fluorescent derivatization of carboxylic acids which allows separation by HPLC.3

Sigma Aldrich - 28553

Other Notes
Coupling reagent used in peptide synthesis1,2

REFERENCES

• J. Am. Chem. Soc. , 97 : 7174 (1975).
• Strecker reaction with aldehydes or ketones in the presence of amines or ammonia gives goodyields ofɑ-amino nitriles: Tetrahedron Lett., 4663 (1979). Pre-formed enamines give the same products: Synthesis, 716 (1979).
• Promotes the formation of amides and esters from amines or alcohols in the presence of, e.g. triethylamine : Tetrahedron, 32, 2211 (1976). The reaction is applicable to peptide synthesis, since little racemization has been observed: J. Am. Chem. Soc., 97, 7174 (1975). The extent of racemization in comparison with other methods has been studied: Chem. Pharm. Bull., 30, 3147 (1982). See Appendix 6. With 2 equivalents of reagent in the absence of a nucleophile, an intermediate 1-(1,1-dicyano)phosphate is formed, leading, on treatment with acid, to the homologated ɑ-hydroxy acid: Tetrahedron Lett., 39, 9209 (1998).
• Can also be used to activate carboxylic acids for the C-acylation of active methylene compounds: J. Org. Chem., 43, 3631 (1978). In the presence of Lewis acids, active methylene compounds such as dimethyl malonate react with the cyanophosphonate itself. The product can be converted to a uracil derivative by reaction with phenyl isocyanate: Chem. Pharm. Bull., 42, 1919 (1994):
  
• Phosphorylating agent for phenols: Synth. Commun., 27, 3035 (1997).
• Activates carboxylic acids towards nucleophiles:
• Thiol esters can be formed under similar conditions: J. Org. Chem., 39, 3302 (1974).