Diethyl cyanophosphonate

• Catalog No.: L14107
• CAS Number: 2942-58-7
• M. F.: C5H10NO3P
• M. W.: 163.111561
• Purity: tech. 90%

SYNONYMS

• Title: 氰基膦酸二乙酯
• IUPAC name: diethyl cyanophosphonate
• IUPAC Traditional name: diethylphosphorocyanidate
• Synonyms: DEPC; Diethyl phosphorocyanidate

DATABASE IDS

• MDL Number: MFCD00010256
• CAS Number: 2942-58-7
• EC Number: 220-936-5
• Beilstein Number: 1768938

PROPERTIES

• Purity: tech. 90%
• Boiling Point: 104-105°C/19mm
• Density: 1.075
• Flash Point: 80°C(176°F)
• Refractive Index: 1.4010
• GHS Hazard statements: H300-H310-H330-H314-H318-H227
• European Hazard Symbols: Highly toxic (T+)
• GHS Precautionary statements: P280-P305+P351+P338-P302+P352-P304+P340-P309-P310
• Risk Statements: 26/27/28-34
• RTECS: TD2500000
• Safety Statements: 26-28-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN2922
• Packing Group: II

REFERENCES

• 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).