Indophenol blue

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Structural formula
Structure of indophenol blue
General
Surname Indophenol blue
other names
  • 4 - {[4- (Dimethylamino) phenyl] imino} naphthalen-1 (4 H ) -one ( IUPAC )
  • Naphthol blue
  • CI 49700
Molecular formula C 18 H 16 N 2 O
Brief description

dark blue powder

External identifiers / databases
CAS number
  • 132-31-0
EC number 205-056-1
ECHA InfoCard 100,004,598
PubChem 67235
ChemSpider 21159500
Wikidata Q34298933
properties
Molar mass 276.3 g mol −1
Physical state

firmly

Melting point

168-170 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319
P: 264-280-302 + 352-332 + 313-362 + 364-305 + 351 + 338-337 + 313
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Indophenol blue is a dye from the group of quinone imine dyes .

Manufacturing

In the first step in the production of indophenol blue, N , N- dimethyl-1,4-phenylenediamine is oxidized with iodine or sodium persulfate to give the quinonediimine . This intermediate reacts with 1-naphthol at the para position to the hydroxyl group in the sense of an electrophilic aromatic substitution . The resulting diarylamine is oxidized to indophenol in the last step:

Structure principle of methine dyes

Structure principle of methine dyes

use

The reaction of an aqueous solution of 1-naphthol and N , N- dimethyl-1,4-phenylenediamine is used as a NADI reagent for the biochemical detection of the enzyme cytochrome c oxidase ( oxidase test ) in bacteria and in histology .

Individual evidence

  1. ↑ a b data sheet Indophenol Blue from Sigma-Aldrich , accessed on July 23, 2019 ( PDF ).
  2. ↑ a b Entry on Indophenol Blue at TCI Europe, accessed on July 23, 2019.
  3. ↑ Ulfrich Nickel: Reactions with Wurster's cations . In: Chemistry in Our Time . tape 12 , no. 3 , 1978, p. 89-98 , doi : 10.1002 / ciuz.19780120305 .
  4. ↑ WL Gaby, C. Hadley: Practical laboratory test for the identification of Pseudomonas aeruginosa , in: J. Bacteriol. 1957, 74 , 356-358, PMID 13475249 , PMC 314647 (free full text).