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Merck

163260

Sigma-Aldrich

4-Chloro-7-nitrobenzofurazan

98%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C6H2ClN3O3
Número de CAS:
Peso molecular:
199.55
Beilstein/REAXYS Number:
614212
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

98%

form

powder

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.

Pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


Certificados de análisis (COA)

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Artículos

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

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