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

L14107 Diethyl cyanophosphonate, tech. 90%

CAS-Nummer
2942-58-7
Synonyme
DEPC
Diethyl phosphorocyanidate

Größe Preis ($) Menge Verfügbarkeit
5g 42,23
25g 119,48
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Diethyl cyanophosphonate, tech. 90%

MDL
MFCD00010256
EINECS
220-936-5

Chemische Eigenschaften

Formel
C5H10NO3P
Molmasse
163.11
Siedepunkt
104-105°/19mm
Flammpunkt
80°(176°F)
Dichte
1.075
Brechungsindex
1.4010
Sensitivität
Moisture Sensitive
Löslichkeit
Hydrolyzes in water.

Anwendungen

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

Bemerkungen

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.

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H300-H310-H330-H314-H318-H227

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

Sicherheitshinweise: P280-P305+P351+P338-P304+P340-P309-P310-P302+P352

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: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water.

Weitere Referenzen

Beilstein
1768938
Gefahrenklasse
8
Verpackungsgruppe
II
Harmonized Tariff Code
2920.90
TSCA
No
RTECS
TD2500000

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