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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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Bis (2, 4-dinitrophenyl) oxalate as a chemiluminescence reagent. Determination of fluorescent compounds by flow injection analysis.
Honda K, et al.
Analytical Chemistry, 55(6), 940-943 (1983)
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
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
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