163260

Sigma-Aldrich

4-Chloro-7-nitrobenzofurazan

98%

Synonim(y):
NBD-chloride, 4-Chloro-7-nitro-1,2,3-benzoxadiazole
Empirical Formula (Hill Notation):
C6H2ClN3O3
Numer CAS:
Masa cząsteczkowa:
199.55
Beilstein/REAXYS Number:
614212
Numer EC:
Numer MDL:
Identyfikator substancji w PubChem:

Poziom jakości

100

próba

98%

mp

97-99 °C (lit.)

rozpuszczalność

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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Opis ogólny

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.

Zastosowanie

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.

Opakowanie

1, 5 g in glass bottle

piktogramy

Exclamation mark

Hasło ostrzegawcze

Warning

Zwroty wskazujące rodzaj zagrożenia

Zwroty wskazujące środki ostrożności

hazcat

Eye Irrit. 2 - Skin Irrit. 2

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Środki ochrony indywidualnej

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

Certyfikat analizy

Świadectwo pochodzenia

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...
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...
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, 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...
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)
Produkty
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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