Bismarck brown Y

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Structural formula
Structure of Bismarck Blue Y
General
Surname Bismarck brown Y
other names
  • 4,4 '- (1,3-phenylenedi-2,1-diazenediyl) di (1,3-benzenediamine) dihydrochloride ( IUPAC )
  • CI Basic Brown 1
  • CI 21000
  • Vesuvin
Molecular formula C 18 H 20 Cl 2 N 8 (dihydrochloride)
External identifiers / databases
CAS number 10114-58-6
EC number 233-314-3
ECHA InfoCard 100.030.273
PubChem 82360
ChemSpider 21241988
Wikidata Q412880
properties
Molar mass 419.32 g mol −1
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bismarck brown Y or Vesuvin is a dye from the series of cationic azo dyes . The dye was named after Otto von Bismarck , the founder and first chancellor of the German Empire . It was discovered in 1863 by Carl Alexander von Martius as the first bisazo dye.

Manufacturing

Bismarck brown Y is synthesized by diazotization and azo coupling of m -phenylenediamine in a one-pot reaction .

properties

Bismarck brown Y has an absorption maximum at 463 nm in water. It is 1–5% (w / v) soluble in water, 1–3% (w / v) in ethanol and 7% (w / v) in ethylene glycol . His pK s value is the fifth

use

Bismarck brown is used in leather , paper and wood dyeing and for the synthesis of polyazo dyes . It is also used in botany for staining plant cell walls and in microbiology for staining bacteria in a modified Gram stain . Robert Koch was able to detect the tubercle bacilli with Bismarck brown.

Similar dyes

  • Bismarck brown R (CI Basic Brown 4) is obtained by an azo coupling using 2,4-diaminotoluene as the diazo and coupling component. It has a redder shade compared to Bismarck brown Y, but otherwise has the same coloring properties. It has also been used on acrylamide gels to optimize the staining of proteins.
  • Bismarck brown G is a mixture of dyes which, in addition to Bismarck brown Y, contains a monoazo dye that is created when simply diazotized m-phenylenediamine is coupled onto itself.

  • Bismarck brown R, CI 21010

  • Bismarck Brown G; PubChem 24181122

Individual evidence

  1. ↑ a b Bismarckbraun Y data sheet from Sigma-Aldrich , accessed on March 13, 2011 ( PDF ).Template: Sigma-Aldrich / name not given
  2. ↑ W. Müller (Ed.): Handbuch der Farbenchemie. Basics, technology, applications . Ecomed Publishing Company; 3. Supplementary delivery 2003; ISBN 3-609-72700-4 ; P. 2.
  3. ^ Wilhelm Strube: The historical way of chemistry, Aulis-Verlag, Cologne 1989, p. 276.
  4. ↑ External identifiers or database links to CI Basic Brown 4 : CAS number: 8005-78-5, EC number: 232-341-8, ECHA InfoCard: 100.029.399 , PubChem : 135516985 , ChemSpider : 26501926 , Wikidata : Q72444823 .
  5. ↑ W. Müller (Ed.): Handbuch der Farbenchemie. Basics, technology, applications . Ecomed Publishing Company; 3. Supplementary delivery 2003; ISBN 3-609-72700-4 ; P. 24 (Chapter 4.7).

literature

  • P. Karrer: Textbook of organic chemistry . 10th edition. Thieme, Stuttgart 1948, p. 514.
  • N. Welsch, CC Liebmann: Colors - nature, technology, art . Spectrum, Heidelberg a. Berlin 2003, p. 204.
  • Richard W. Horobin, JA Kiernan, and John A. Kiernan: Conn's Biological Stains: A Handbook of Dyes, Stains and Fluorochromes for Use in Biology and Medicine . Garland Pub, 10th edition, 2002; ISBN 1-85996-099-5 ; Pp. 139-140.