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2942-58-7 - Diethyl cyanophosphonate, tech. 90% - DEPC - Diethyl phosphorocyanidate - L14107 - Alfa Aesar

L14107 Diethyl cyanophosphonate, tech. 90%

CAS Number
2942-58-7
Synonyms
DEPC
Diethyl phosphorocyanidate

Size Price ($) Quantity Availability
5g 41.80
25g 118.00
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Diethyl cyanophosphonate, tech. 90%

MDL
MFCD00010256
EINECS
220-936-5

Chemical Properties

Formula
C5H10NO3P
Formula Weight
163.11
Boiling Point
104-105°/19mm
Flash Point
80°(176°F)
Density
1.075
Refractive Index
1.4010
Sensitivity
Moisture Sensitive
Solubility
Hydrolyzes in water.

Applications

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

Notes

It is sensitive to moisture. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature is 2 - 8°C.

Literature References

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):

GHS Hazard and Precautionary Statements

Hazard Statements: H227-H300-H310-H330-H314-H318

Combustible liquid. Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P280-P305+P351+P338-P304+P340-P309-P310a-P302+P352a

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF exposed or if you feel unwell: IF ON SKIN:

Other References

Beilstein
1768938
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2920.90
TSCA
No
RTECS
TD2500000

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