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472565

Sigma-Aldrich

Diethyl cyanophosphonate

90%

Synonym(s):

DEPC, Diethyl phosphoryl cyanide

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About This Item

Linear Formula:
(CH3CH2O)2P(O)CN
CAS Number:
2942-58-7
Molecular Weight:
163.11
Beilstein:
1768938
EC Number:
220-936-5
MDL number:
MFCD00010256
UNSPSC Code:
12352100
PubChem Substance ID:
24870809

Assay

90%

refractive index

n20/D 1.403 (lit.)

bp

104-105 °C/19 mmHg (lit.)

density

1.075 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOP(=O)(OCC)C#N

InChI

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

InChI key

ZWWWLCMDTZFSOO-UHFFFAOYSA-N

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General description

Diethyl cyanophosphonate (DCNP, a Tabun mimic, DECP) is a nerve agent simulant. Its detection by using fluorescein, a reversible fluorescent sensor, has been reported. Its degradation in the presence of suitable organocatalysts (different amines, aminoalcohols and glycols) has been studied.

Application

Coupling reagent for peptide synthesis. Reagent for the phosphorylation of phenols. Activating agent for fluorescent derivatization of carboxylic acids which allows separation by HPLC.

Other Notes

Contains triethyl phosphate

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H314

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1B

Supplementary Hazards

EUH032

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

176.0 °F - closed cup

Flash Point(C)

80 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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T C Bruice et al.
Proceedings of the National Academy of Sciences of the United States of America, 89(5), 1700-1704 (1992-03-01)
The structures of the compounds we call 3a, 3b, and 3c-compounds that incorporate (i) the tripyrrole peptide of the minor-groove-binding distamycin class of compounds and (ii) polyamine ligands that extend from the minor groove and can interact with phosphodiester bonds--were
Andrea Barba-Bon et al.
Journal of hazardous materials, 298, 73-82 (2015-05-26)
We report herein a study of the hydrolysis of Tabun mimic DCNP in the presence of different amines, aminoalcohols and glycols as potential suitable organocatalysts for DCNP degradation. Experiments were performed in CD3CN in the presence of 5% D2O, which
T Momose et al.
Lipids, 32(7), 775-778 (1997-07-01)
A simple and efficient method for the synthesis of taurine- and glycine-conjugated bile acids is described. The condensation reaction was achieved by the simple mixing of unconjugated bile acid (1.0 eq.), taurine (2.0 eq.) (or glycinate ester), diethyl phosphorocyanidate (1.2
Yoon Jeong Jang et al.
The Analyst, 139(7), 1614-1617 (2014-02-22)
Herein, we present fluorescein as a reversible fluorescent sensor for nerve agent simulants diethylchlorophosphate (DCP), diethyl methylphosphonate (DEMP), and diethyl cyanophosphonate (DECP). The superoxide allows for an "off-on" mechanism to regenerate fluorescein. The order of decrease in fluorescence intensity for
Jingfeng Rong et al.
Cell cycle (Georgetown, Tex.), 19(12), 1478-1491 (2020-05-07)
As some evidence has demonstrated the role of microRNA-221 (miR-221) on coronary heart disease (CHD), the aim of the present study was to investigate the effect of miR-221-3p on CHD via regulating NLRP3/ASC/pro-caspase-1 inflammasome pathway. Sixty CHD patients and 60
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