Bindschedler's green

from Wikipedia, the free encyclopedia
Structural formula
Structure of Bindschedler's Green
General
Surname Bindschedler's green
other names
  • [4- (4-Dimethylamino-phenylimino) -cyclohexa-2,5-dienylidene] -dimethyl-ammonium chloride
  • CI 49405
Molecular formula C 16 H 20 ClN 3
External identifiers / databases
CAS number 4486-05-9
EC number 224-773-0
ECHA InfoCard 100.022.522
PubChem 73516
ChemSpider 66201
Wikidata Q863659
properties
Molar mass 289.81 g mol −1
Physical state

firmly

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bindschedler's green is a green dye from the indamine group . It is produced by condensation of N , N -dimethylaniline with 4-nitroso- N , N -dimethylaniline or by oxidative coupling of N , N -dimethylaniline with 4-amino- N , N -dimethylaniline with sodium dichromate as the oxidizing agent and bears the name of his Explorer Robert Bindschedler .

Bindschedler's green can be used for the quantitative determination of hydrogen sulfide , as it reacts with this completely to form methylene blue , which can be detected photometrically at 680 nm. The absorption maximum of Bindschedler's green is 727  nm . This absorption band can be shifted further into the longer-wave range by modifications. Various indamine dyes with a basic structure derived from Bindschedler's green absorb in the near infrared range ( NIR ).

Various assays have been developed on the basis of Bindschedler's green , for example a cytotoxicity assay. The compound can also be used to measure the activity of dehydrogenase .

Individual evidence

  1. ↑ a b data sheet BINDSCHEDLERS GREEN, INDICATOR GRADE from Sigma-Aldrich , accessed on May 13, 2011 ( PDF ).
  2. ↑ Entry on indamine. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
  3. ↑ H. Wieland, in: Ber. d. dt. Chem. Ges. 1915 , 48 , p. 1078.
  4. ↑ HJ Shine, RL Snell, JC Trisler: Nature of Bindschedler's Green: preparation for analysis of hydrazo compounds , in: Anal. Chem. 1958 , 30 , pp. 383-384.
  5. ^ A b J. Griffiths, R. Cox: Light absorption and stability properties of some near-IR indamine dyes related to Bindschedler's green , in: Dyes and Pigments 1999 , 42 , pp. 29-34.
  6. ↑ F. Tietze, T. Eicher, reactions and syntheses in the organic-chemical internship and research laboratory , 2nd edition, ISBN 978-3-527-30874-3 (paper), ISBN 978-3-527-60171-4 (online )
  7. ↑ T. Schödl: Sulphide-Quinone Reductase (SQR) from Aquifex aeolicus: gene synthesis, expression, purification and biochemical characterization , dissertation, Regensburg 2003 , p. 65
  8. ↑ K. Takagi in: A sensitive colorimetric assay for polyamines in erythrocytes using oat seedling polyamine oxidase , in: Clin. Chim. Acta 2004 , 340 , pp. 219-227.
  9. ↑ S. Yamashoji: A cytotoxicity assay with Bindschedler's green leuco base , in: Anal. Biochem. 1996 , 240 , pp. 310-312; PMID 8811930
  10. ↑ MD Smith, CL Olson: Differential amperometric measurement of serum lactate dehydrogenase activity using Bindschedler's green , in: Anal. Chem. 1974 , 46 , pp. 1544-1547; PMID 4412813