CAS 2942-58-7|diethylphosphorocyanidate|Diethyl cyanophosphonate|diethyl cyanophosphonate|(Diethoxyphosphoryl)cyanide|Diethyl phosphorocyanidate|DEPC|Diethyl cyanophosphonate|氰基膦酸二乙酯|diethyl ...

General Information

Structure

Molecular Formula

C₅H₁₀NO₃P

Molecular Mass

163.111561

Exact Mass

163.03982982

Charge

InChI

InChI=1S/C5H10NO3P/c1-3-8-10(7,5-6)9-4-2/h3-4H2,1-2H3

InChIKey

ZWWWLCMDTZFSOO-UHFFFAOYSA-N

Canonic Smiles

CCOP(=O)(C#N)OCC

Isomeric Smiles

P(=O)(C#N)(OCC)OCC

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

0.63806987

LogD (pH = 7.4)

0.63806987

Log P

0.63806987

Molar Refractivity

36.9701

Polarizability

14.597984

Polar Surface Area

59.32

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

(Diethoxyphosphoryl)cyanideDiethyl phosphorocyanidateDiethyl cyanophosphonateDiethyl cyanophosphonateDEPC氰基膦酸二乙酯diethyl phosphorocyanidate氰代磷酸二乙酯Diethyl phosphoryl cyanide

IUPAC name

diethyl cyanophosphonate

IUPAC Traditional name

diethylphosphorocyanidate

Names and Identifiers

Registration numbers

PubChem CID

76257

PubChem SID

1620746672487080924857217

CAS Number

Beilstein Number

EC Number

MDL Number

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02150888

Coupling reagent for peptide synthesis.

Sigma Aldrich

472565

Other Notes
Contains triethyl phosphate
Packaging
5, 25, 100 mL in glass bottle
Application
Coupling reagent for peptide synthesis.1 Reagent for the phosphorylation of phenols.2 Activating agent for fluorescent derivatization of carboxylic acids which allows separation by HPLC.3

28553

Other Notes
Coupling reagent used in peptide synthesis1,2

Molecule Details

References

PubChem Literature

From Data Sources

• J. Am. Chem. Soc. , 97 : 7174 (1975).

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

(Diethoxyphosphoryl)cyanideDiethyl phosphorocyanidateDiethyl cyanophosphonateDiethyl cyanophosphonateDEPC氰基膦酸二乙酯diethyl phosphorocyanidate氰代磷酸二乙酯Diethyl phosphoryl cyanide

IUPAC name

diethyl cyanophosphonate

IUPAC Traditional name

diethylphosphorocyanidate

Registration numbers

PubChem CID

76257

PubChem SID

1620746672487080924857217

CAS Number

2942-58-7

Beilstein Number