163260
4-Chloro-7-nitrobenzofurazan
98%
Synonym(s):
4-Chloro-7-nitro-1,2,3-benzoxadiazole, NBD-chloride
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About This Item
Empirical Formula (Hill Notation):
C6H2ClN3O3
CAS Number:
Molecular Weight:
199.55
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
233-496-4
Beilstein/REAXYS Number:
614212
MDL number:
Assay:
98%
Form:
powder
InChI key
IGHBXJSNZCFXNK-UHFFFAOYSA-N
InChI
1S/C6H2ClN3O3/c7-3-1-2-4(10(11)12)6-5(3)8-13-9-6/h1-2H
SMILES string
[O-][N+](=O)c1ccc(Cl)c2nonc12
assay
98%
form
powder
mp
97-99 °C (lit.)
solubility
chloroform: soluble 50 mg/mL, clear to slightly hazy, faintly yellow to yellow
functional group
chloro, nitro
Quality Level
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Application
4-Chloro-7-nitrobenzofurazan (NBD-chloride) was used in the following studies:
- Synthesis of fluorescent phospholipid-derivative, NBD-didecanoylphosphatidylethanolamine
- Synthesis of functionalized hydroxynaphthofurazan.
- Spectrophotometric and spectrofluorometric determination of clemastine hydrogen fumarate, loratadine, losartan potassium and ramipril in pharmaceutical formulations.
- Synthesis of 7-nitrobenzofurazan (NBD)-labeled maleimide, via Diels-Alder reaction.
General description
4-Chloro-7-nitrobenzofurazan (NBD-Cl) is a highly sensitive chromogenic and fluorogenic reagent. It is reported to react spontaneously with trans-1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene (Danishefsky′s diene), to afford regioselectively the silyl enol ether, via normal electron-demand Diels-Alder (NEDDA) reaction. A study of the molecular structure, vibrational spectra and NBO (Natural Bond Orbital) analysis of NBD–Cl has been undertaken. Its utility as a pre-column derivatization agent has been examined.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Molecular structure, vibrational, UV and NBO analysis of 4-chloro-7-nitrobenzofurazan by DFT calculations.
Kurt M, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 79(5), 1162-1170 (2011)
Gholamreza Bahrami et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 850(1-2), 400-404 (2007-01-02)
A new, sensitive and simple high-performance liquid chromatographic method for analysis of topiramate, an antiepileptic agent, using 4-chloro-7-nitrobenzofurazan as pre-column derivatization agent is described. Following liquid-liquid extraction of topiramate and an internal standard (amlodipine) from human serum, derivatization of the
Marco Filice et al.
Organic & biomolecular chemistry, 9(15), 5535-5540 (2011-06-23)
Lipase B from Candida antarctica (CAL-B) has been site-directedly modified by the introduction of a trans,trans-hexadiene moiety onto lipase molecules, identified by MALDI-TOF. This modification on CAL-B permitted its immobilization on Q-Sepharose supports in excellent yields (>95%) when native lipase
4-Chloro-7-nitrobenzofurazan as a Diels-Alder reagent. A facile access to highly functionalized naphthofurazans.
Vichard D, et al.
Tetrahedron Letters, 42(43), 7571-7574 (2001)
Emmanuel C Gorospe et al.
Gastrointestinal endoscopy, 76(5), 933-938 (2012-09-18)
There are currently 2 existing confocal laser endomicroscopy (CLE) platforms: probe-based CLE (pCLE) and endoscope-based CLE (eCLE) systems, each with its own criteria for identifying dysplasia in Barrett's esophagus (BE). The diagnostic performance of these 2 systems has not been
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