Substance
ID:737280
Names and Identifiers
IUPAC Traditional name
diethylphosphorocyanidate
Synonyms
Diethyl phosphorocyanidateDiethyl cyanophosphonate氰基膦酸二乙酯DEPC
IUPAC name
diethyl cyanophosphonate
Registration numbers
Beilstein Number
EC Number
CAS Number
MDL Number
Properties
Physical Property
Density
1.075
Flash Point
80°C(176°F)
Boiling Point
104-105°C/19mm
Refractive Index
1.4010
Safety Information
GHS Hazard statements
H300-H310-H330-H314-H318-H227
GHS Precautionary statements
P280-P305+P351+P338-P302+P352-P304+P340-P309-P310
European Hazard Symbols
Highly toxic (T+)GHS Pictograms
Acute toxicity (oral, dermal, inhalation), categories 1,2,3
Corrosive to metals, category 1
Skin corrosion, categories 1A,1B,1C
Serious eye damage, category 1
Storage Warning
Moisture Sensitive
UN Number
UN2922
Safety Statements
26-28-36/37/39-45
Packing Group
II
RTECS
TD2500000
Hazard Class
8
Risk Statements
26/27/28-34
TSCA Listed
否
Product Information
Purity
tech. 90%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• 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).
• Thiol esters can be formed under similar conditions: J. Org. Chem., 39, 3302 (1974).
• 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).
• Activates carboxylic acids towards nucleophiles:
• 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).