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163260

Sigma-Aldrich

4-Chloro-7-nitrobenzofurazan

98%

Synonym(s):

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

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About This Item

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
Pricing and availability is not currently available.

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

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General description

4-Chloro-7-nitrobenzofurazan (NBD-Cl) is a highly sensitive chromogenic and fluorogenic reagent.[1] 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.[1] A study of the molecular structure, vibrational spectra and NBO (Natural Bond Orbital) analysis of NBD–Cl has been undertaken.[2] Its utility as a pre-column derivatization agent has been examined.[3][4]

Application

4-Chloro-7-nitrobenzofurazan (NBD-chloride) was used in the following studies:
  • Synthesis of fluorescent phospholipid-derivative, NBD-didecanoylphosphatidylethanolamine[5]
  • Synthesis of functionalized hydroxynaphthofurazan.[6]
  • Spectrophotometric and spectrofluorometric determination of clemastine hydrogen fumarate, loratadine, losartan potassium and ramipril in pharmaceutical formulations.[1]
  • Synthesis of 7-nitrobenzofurazan (NBD)-labeled maleimide, via Diels-Alder reaction.[7]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4346
STBL4345
STBL0661
STBK4603
STBJ6389

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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
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)
Junjie Yao et al.
NeuroImage, 64, 257-266 (2012-09-04)
We have demonstrated the feasibility of imaging mouse brain metabolism using photoacoustic computed tomography (PACT), a fast, noninvasive and functional imaging modality with optical contrast and acoustic resolution. Brain responses to forepaw stimulations were imaged transdermally and transcranially. 2-NBDG, which
Parallel dip-pen nanolithography using spore- and colloid-terminated cantilevers.
Marcus A Kramer et al.
Small (Weinheim an der Bergstrasse, Germany), 8(24), 3791-3794 (2012-08-18)
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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. It is also referred to as a cycloaddition.

Diels–Alder Reaction

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.

Diels–Alder Reaction

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.

Diels–Alder Reaction

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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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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