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325376

Sigma-Aldrich

Bis(2,4-dinitrophenyl) oxalate

98%

Synonym(s):

2,4-Dinitrophenyl oxalate, DNPO, Oxalic acid bis(2,4-dinitrophenyl) ester

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About This Item

Linear Formula:
[-CO2C6H3(NO2)2]2
CAS Number:
16536-30-4
Molecular Weight:
422.22
Beilstein:
2318321
MDL number:
MFCD00010712
UNSPSC Code:
12352100
PubChem Substance ID:
24859504
NACRES:
NA.22

Assay

98%

mp

189-190 °C (lit.)

SMILES string

[O-][N+](=O)c1ccc(OC(=O)C(=O)Oc2ccc(cc2[N+]([O-])=O)[N+]([O-])=O)c(c1)[N+]([O-])=O

InChI

1S/C14H6N4O12/c19-13(29-11-3-1-7(15(21)22)5-9(11)17(25)26)14(20)30-12-4-2-8(16(23)24)6-10(12)18(27)28/h1-6H

InChI key

CBZOGAWUNMFXFQ-UHFFFAOYSA-N

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General description

Bis(2,4-dinitrophenyl) oxalate (DNPO) is a chemiluminescence reagent. Chemiluminescence produced in the oxidation of DNPO by hydrogen peroxide in the presence of a polycyclic aromatic hydrocarbon was monitored by spectroscopic methods. The kinetics of the imidazole-catalyzed decomposition of DNPO was investigated by the stopped-flow technique.

Application

Bis(2,4-dinitrophenyl) oxalate was used in detection of fluorescent compound dansylalanine in buffer solution by flow injection analysis.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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M B Talawar et al.
Journal of hazardous materials, 124(1-3), 153-164 (2005-06-28)
This paper reviews the recent work done on the synthesis as well as characterization of dinitrogen pentoxide (DNPO). The physico-chemical characteristics of DNPO are also discussed. The review brings out the key aspects of N2O5 technology with relevance to realize
José Antonio Murillo Pulgarín et al.
Analytica chimica acta, 691(1-2), 76-82 (2011-04-05)
Kinetic and spectroscopic methods were used in combination in this work to develop a new analytical tool for use in chemiluminescence detection processes. Specifically, time-resolved chemiluminescence was used jointly with a stopped-flow assembly in order to monitor the chemiluminescence produced
Andrew G. Hadd et al.
The Journal of organic chemistry, 61(8), 2657-2663 (1996-04-19)
The kinetics of the imidazole-catalyzed decomposition of bis(2,4,6-trichlorophenyl) oxalate (TCPO) and bis(2,4-dinitrophenyl) oxalate (DNPO) was investigated by the stopped-flow technique. Pseudo-first-order rate constants were determined as a function imidazole concentration in the temperature range 6-45 degrees C by fitting the
T Kawasaki et al.
Biomedical chromatography : BMC, 4(3), 113-118 (1990-05-01)
Dopamine (DA), norepinephrine (NE) and 3,4-dihydroxybenzylamine (DHBA) are converted to highly fluorescent cyanobenz[f]isoindole (CBI) derivatives by reacting these amines with naphthalene-2,3-dicarboxaldehyde in the presence of cyanide ion. Femtomole amounts of these CBI derivatives separated by reverse-phase high performance liquid chromatography
W Baeyens et al.
Journal of bioluminescence and chemiluminescence, 5(1), 13-23 (1990-01-01)
Bis(2,4,6-trichlorophenyl) oxalate (TCPO)-hydrogen-peroxide-generated chemiluminescence (CL) of four dansyl amino acids has been used as a model system for the optimization of a detection system in reversed-phase high-performance liquid chromatography. Dansylated alanine, glutamic acid, methionine, and norleucine were subjected to peroxyoxalate
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