Bismarck brown Y

Source: Wikipedia, the free encyclopedia.
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 Edit this at Wikidata
  • InChI=1S/C18H18N8/c19-11-4-6-17(15(21)8-11)25-23-13-2-1-3-14(10-13)24-26-18-7-5-12(20)9-16(18)22/h1-10H,19-22H2/b25-23+,26-24+ ☒N
    Key: BDFZFGDTHFGWRQ-OGGGYYITSA-N ☒N
  • InChI=1/C18H18N8/c19-11-4-6-17(15(21)8-11)25-23-13-2-1-3-14(10-13)24-26-18-7-5-12(20)9-16(18)22/h1-10H,19-22H2/b25-23+,26-24+
    Key: BDFZFGDTHFGWRQ-OGGGYYITBR
  • CC1=C(C=C(C=C1)N=NC2=C(C=C(C(=C2)C)N)N)N=NC3=C(C=C(C(=C3)C)N)N
  • N(=N/c1ccc(cc1N)N)\c3cccc(/N=N/c2ccc(N)cc2N)c3
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 checkY☒N ?)

Bismarck brown Y also called

staining tissues.[2]

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

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

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

acid-fast
microorganisms.

References

  1. ^ a b c Lillie, Ralph Dougall (1977). H. J. Conn's Biological stains (9th ed.). Baltimore: Williams & Wilkins. pp. 692p.
  2. ^
    ISBN 3527306730
    .
  3. doi:10.15547/tjs.2017.03.001
    .
  4. ^ The Chemical Formulary. David Van Nostrand Company Inc. 1933. p. 86.
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