4-Fluoro-7-nitrobenzofurazan

Last updated
NBD-F [1]
4-fluoro-7-nitrobenzofurazan chemical structure.svg
Names
IUPAC name
4-fluoro-7-nitro-2,1,3-benzoxadiazole
Other names
NBD-F
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.162.766 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 634-820-0
PubChem CID
  • InChI=1S/C6H2FN3O3/c7-3-1-2-4(10(11)12)6-5(3)8-13-9-6/h1-2H
    Key: PGZIDERTDJHJFY-UHFFFAOYSA-N
  • C1=C(C2=NON=C2C(=C1)F)[N+](=O)[O-]
Properties
C6H2FN3O3
Molar mass 183.10 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Fluoro-7-nitrobenzofurazan (NBD-F) is a fluorogenic, amine labeling dye that is not fluorescent itself, but covalently reacts with secondary or primary amines to form a fluorescently labeled product. [2] It and other fluorogenic benzofurans (i.e. NBD-Cl) are used for derivitization in HPLC applications. [3] After the fluorogenic reaction, it can be detected with an excitation wavelength of 470 nm (blue) and an emission wavelength of 530 nm (green), enabling an HPLC limit of detection of 10 fmol. [4]

See also

References

  1. ↑ "4-Fluoro-7-nitrobenzofurazan". PubChem. National Library of Medicine. Retrieved 11 March 2023.
  2. ↑ Stoyanov, Alexander V.; Ahmadzadeh, Hossein; Krylov, Sergey N. (2002-11-25). "Heterogeneity of protein labeling with a fluorogenic reagent, 3-(2-furoyl)quinoline-2-carboxaldehyde". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 780 (2): 283–287. doi:10.1016/s1570-0232(02)00535-4. ISSN   1570-0232. PMID   12401353.
  3. ↑ Maroulis, Marios; Monemvasios, Ioannis; Vardaka, Elisabeth; Rigas, Pantelis (2008). "Determination of domoic acid in mussels by HPLC with post-column derivatization using 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl) and fluorescence detection". Journal of Chromatography B. 876 (2). Elsevier BV: 245–251. doi:10.1016/j.jchromb.2008.10.053. ISSN   1570-0232. PMID   19026599.
  4. ↑ Watanabe, Yoshihiko; Imai, Kazuhiro (1981). "High-performance liquid chromatography and sensitive detection of amino acids derivatized with 7-fluoro-4-nitrobenzo-2-oxa-1,3-diazole". Analytical Biochemistry. 116 (2). Elsevier BV: 471–472. doi:10.1016/0003-2697(81)90390-0. ISSN   0003-2697. PMID   7316179.
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