163260

4-Chloro-7-nitrobenzofurazan

98%

• Synonym(s): 4-Chloro-7-nitro-1,2,3-benzoxadiazole, NBD-chloride
• Empirical Formula (Hill Notation): C₆H₂ClN₃O₃
• CAS Number: 10199-89-0
• Molecular Weight: 199.55
• Beilstein: 614212
• EC Number: 233-496-4
• MDL number: MFCD00005808
• UNSPSC Code: 12352100
• PubChem Substance ID: 24849737
• NACRES: NA.22

Properties

• Quality Level: 100
• 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

Description

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319
• Precautionary Statements: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• 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