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163260

Sigma-Aldrich

4-Chloro-7-nitrobenzofurazan

98%

Synonym(s):
NBD-chloride, 4-Chloro-7-nitro-1,2,3-benzoxadiazole
Empirical Formula (Hill Notation):
C6H2ClN3O3
CAS Number:
Molecular Weight:
199.55
Beilstein:
614212
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

98%

mp

97-99 °C (lit.)

solubility

chloroform: soluble 50 mg/mL, clear to slightly hazy, faintly yellow to yellow

SMILES string

[O-][N+](=O)c1ccc(Cl)c2nonc12

InChI

1S/C6H2ClN3O3/c7-3-1-2-4(10(11)12)6-5(3)8-13-9-6/h1-2H

InChI key

IGHBXJSNZCFXNK-UHFFFAOYSA-N

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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.

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.

Packaging

1, 5 g in glass bottle

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
Gholamreza Bahrami et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 857(2), 322-326 (2007-08-21)
A sensitive and rapid high-performance liquid chromatographic method for the analysis of fluvoxamine, a selective serotonin reuptake inhibitor in human serum, is described using 4-chloro-7-nitrobenzofurazan as pre-column derivatization agent. The drug and an internal standard (fluoxetine) were extracted from 0.25...
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)

Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

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