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163260 Aldrich

4-Chloro-7-nitrobenzofurazan

98%

Synonym: 4-Chloro-7-nitro-1,2,3-benzoxadiazole, NBD-chloride

  • CAS Number 10199-89-0

  • Empirical Formula (Hill Notation) C6H2ClN3O3

  • Molecular Weight 199.55

  •  Beilstein Registry Number 614212

  •  EC Number 233-496-4

  •  MDL number MFCD00005808

  •  PubChem Substance ID 24849737

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Properties

Related Categories Biochemicals and Reagents, Building Blocks, Chemical Synthesis, Derivatization agents, Fluorescent Probes, Labels, Particles and Stains,
InChI Key   IGHBXJSNZCFXNK-UHFFFAOYSA-N
assay   98%
mp   97-99 °C (lit.)
solubility   chloroform: soluble 50 mg/mL, clear to slightly hazy, faintly yellow to yellow

Description

Packaging

1, 5 g in glass bottle

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
DF8002400

Documents

Certificate of Analysis

Certificate of Origin


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Protocols & Articles

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 vi...
Keywords: Addition reactions, Asymmetric synthesis, Building blocks, Catalysis, Cycloadditions, Diels-Alder reaction, Immobilization

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