Bismarck brown Y

Bismarck brown Y also called C.I. 21000[1] and C.I. Basic Brown 1,[1] is a diazo dye with the idealized formula [(H2N)2C6H3N2]2C6H4. The dye is a mixture of closely related compounds. It was one of the earliest azo dyes, being described in 1863. It is used in histology for staining tissues.[2]

Bismarck brown Y
Names
Other names
Bismarck brown
Manchester brown
Phenylene brown
Basic Brown 1
C.I. 21000
Vesuvine BA
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.030.273
Properties
C18H18N8·2HCl
Molar mass 419.31 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis

The dye is simple to prepare because the diamine serves both as a source of the diazonium cation and as the coupling partner in the azo coupling reaction. The synthesis is thought to start with double diazotization of 1,3-phenylenediamine:

(H2N)2C6H4 + 2 H+ + 2 HNO2 → [C6H4(N2)2]2+ + 2 H2O

It is assumed that this bis(diazonium) ion subsequently attacks two equivalents of 1,3-phenylenediamine:

2 (H2N)2C6H4 + [C6H4(N2)2]2+ → 2 H+ + [(H2N)2C6H3N2]2C6H4

In some cases, toluenediamines are used in addition to the phenylenediamine. Furthermore the resulting dye is thought to consist of oligomers with three or more diazo groups.[2]

Uses

Bismarck brown Y stains acid mucins to yellow color. It also stains mast cell granules brown.[3] It can be used with live cells. It is also used to stain cartilage in bone specimens, as one of Kasten's Schiff-type reagents in the periodic acid-Schiff stain to stain cellulose, and in Feulgen stain to stain DNA. It was more common in the past; today it is partially replaced by other stains. It has also been used to give soap an amber color in the past.[4]

Bismarck brown Y is a constituent of Papanicolaou stain.[1]

It can also be used as a counterstain for Victoria blue R for staining of acid-fast microorganisms.

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References
  1. Lillie, Ralph Dougall (1977). H. J. Conn's Biological stains (9th ed.). Baltimore: Williams & Wilkins. pp. 692p.
  2. Booth, Gerald (2000). "Dyes, General Survey". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_073.
  3. Tomov, Nikola; Dimitrov, Nikolay (2017). "Modified Bismarck brown staining for demonstration of soft tissue mast cells" (PDF). Trakia Journal of Sciences. 3: 195–197.
  4. The Chemical Formulary. David Van Nostrand Company Inc. 1933. p. 86.
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