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Diethyl cyanophosphonate is used for peptide synthesis. and for the phosphorylation of phenols. It is also used as an activating agent for fluorescent derivatization of carboxylic acids which allows separation by HPLC, to activate carboxylic acids for the C-acylation of active methylene compounds and as a reagent for the phosphorylation of phenols. It promotes the formation of amides and esters from amines or alcohols in the presence of, e.g. triethylamine, activates carboxylic acids towards nucleophiles
Angel Guzmána.; Eduardo Diaz. A Convenient Method for the Phosphorylation of Phenols with Diethyl Cyanophosphonate. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry. 1997, 27 (17), 3035-3038.
Kouta Masutani.; Tomofumi Minowa.; Yoshiaki Hagiwara.; Teruaki Mukaiyama. Cyanation of Alcohols with Diethyl Cyanophosphonate and 2,6-Dimethyl-1,4-benzoquinone by a New Type of Oxidation-Reduction Condensation. Bulletin of the Chemical Society of Japan. 2006, 79 (7), 1106-1117.
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).
Phosphorylating agent for phenols: Synth. Commun., 27, 3035 (1997).
Activates carboxylic acids towards nucleophiles:
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).
Thiol esters can be formed under similar conditions: J. Org. Chem., 39, 3302 (1974).
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):
Hazard Statements: H227-H300-H310-H314-H330-H335
Combustible liquid. Fatal if swallowed. Fatal in contact with skin. Causes severe skin burns and eye damage. Fatal if inhaled. May cause respiratory irritation.
Precautionary Statements: P210-P235-P260-P262-P264b-P270-P271-P280-P284-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Do not breathe dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. Wear respiratory protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant