163260
4-Chloro-7-nitrobenzofurazan
98%
동의어(들):
4-Chloro-7-nitro-1,2,3-benzoxadiazole, NBD-chloride
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제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C6H2ClN3O3
CAS 번호:
Molecular Weight:
199.55
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
233-496-4
Beilstein/REAXYS Number:
614212
MDL number:
Assay:
98%
Form:
powder
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
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
저장 등급
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
문서
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.
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