4-chloro-7-nitrobenzo-2-oxa-1,3-diazole

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Structural formula
Structure of NBD-Cl
General
Surname 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole
other names
  • 7-chloro-4-nitro-benzofurazan
  • 4-chloro-7-nitrobenzofurazan
  • NBD-Cl
Molecular formula C 6 H 2 ClN 3 O 3
Brief description

light yellow powder

External identifiers / databases
CAS number 10199-89-0
EC number 233-496-4
ECHA InfoCard 100.030.439
PubChem 25043
Wikidata Q229939
properties
Molar mass 199.55 g mol −1
Physical state

firmly

Melting point

97-99 ° C

solubility

soluble in DMSO , dimethylformamide , methanol , acetonitrile and chloroform

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301
P: 301 + 310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-chloro-7-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl) or 4-chloro-7-nitro-2,1,3-benzoxadiazole , sometimes also 4-chloro-7-nitrobenzofurazan is a Derivatizing reagent for amino acids , carboxylic acids , phenols and thiols . It is also used as an immersion reagent for thin-layer chromatography plates to make said substances visible on the plate (with sodium acetate solution / NBD-Cl solution).

Reaction course

Derivatization is always on polar hydrogen - atom .

Pyrithione (as a sodium - salt and sodium omadine), a fungicide and bactericide is to HPLC derivatized analysis, since the pyrithione itself much too polar for analysis on a reversed-phase HPLC column (C18) is, next to the dead time the system would elute (exception: eluent with ion pair chromatography reagent).

Reaction of NBD-Cl with pyrithione (?)

The detection is done either by UV absorption at 330 nm or by UV fluorescence detection with excitation at 337 nm and the emission measurement for amine NBD derivatives at 464 mn / 512 nm. The fluorescence detection is more specific and does not produce as much interference.

literature

  • PB Ghosh, MW Whitehouse: 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole: a new fluorigenic reagent for amino acids and other amines. In: The Biochemical journal. Volume 108, Number 1, June 1968, pp. 155-156, PMID 5657448 . PMC 1198782 (free full text).

Individual evidence

  1. ↑ a b c d Data sheet 4-Chloro-7-nitrobenzofurazan from Sigma-Aldrich , accessed on March 17, 2015 ( PDF ).
  2. ↑ FluoProbes data sheet : NBD (PDF; 151 kB) from Interchim, accessed on November 7, 2012.