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
Beilstein:
614212
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
form:
powder
Assay:
98%
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Quality Level
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
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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4-Chloro-7-nitrobenzofurazan as a Diels-Alder reagent. A facile access to highly functionalized naphthofurazans.
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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
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