Bismarck brown Y

Bismarck brown Y
Names
	Other names Bismarck brown ; Manchester brown ; Phenylene brown ; Basic Brown 1 ; C.I. 21000; Vesuvine BA
Identifiers
CAS Number	8005-77-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	13374 ;
ECHA InfoCard	100.030.273
PubChem CID	13981;
	InChI 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+ Key: BDFZFGDTHFGWRQ-OGGGYYITSA-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;
	SMILES 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
Chemical formula	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).
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	Infobox references

Bismarck brown Y 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.^[1]

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.^[1]

Uses

Bismarck brown Y stains acid mucins to yellow color. It also stains mast cell granules brown.^[2] 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.

Bismarck brown Y is a constituent of Papanicolaou stains.

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

References

1 2 Booth, Gerald (2000). "Dyes, General Survey". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_073.
↑ Tomov, Nikola; Dimitrov, Nikolay (2017). "Modified Bismarck brown staining for demonstration of soft tissue mast cells" (PDF). Trakia Journal of Sciences. 3: 195–197.

Names

Other names Bismarck brown Manchester brown Phenylene brown Basic Brown 1 C.I. 21000 Vesuvine BA
Identifiers
CAS Number	8005-77-4^N
3D model (JSmol)	Interactive image Interactive image
ChemSpider	13374^N
ECHA InfoCard	100.030.273
PubChem CID	13981
InChI 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
SMILES 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
Chemical formula	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

Bismarck brown Y

Synthesis

Uses

References

See also