“Bismarck brown Y”的意思、由来-开放百科全书

词条

Bismarck brown Y

释义

Synthesis
Uses
References
See also

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 459979781
| ImageFile = BismarckBrownNeutral.png
| ImageSize = 300 px
| IUPACName =
| OtherNames = Bismarck brown
Manchester brown
Phenylene brown
Basic Brown 1
C.I. 21000
Vesuvine BA
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 13374
| 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+
| InChIKey = BDFZFGDTHFGWRQ-OGGGYYITBR
| SMILES1 = N(=N/c1ccc(cc1N)N)\\c3cccc(/N=N/c2ccc(N)cc2N)c3
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = BDFZFGDTHFGWRQ-OGGGYYITSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 8005-77-4
| PubChem = 13981
| 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
|Section2={{Chembox Properties
| Formula = C₁₈H₁₈N₈·2HCl
| MolarMass = 419.31 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}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. It has also been used to give soap an amber color in the past.^[3]

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. ^¹{{cite encyclopedia|last=Booth|first=Gerald|title=Dyes, General Survey|year=2000|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a09_073}}
2. ^{{Cite journal|last=Tomov|first=Nikola|last2=Dimitrov|first2=Nikolay|date=2017|title=Modified Bismarck brown staining for demonstration of soft tissue mast cells|url=http://tru.uni-sz.bg/tsj/Vol15_N3_2017/2_N.Tomov.pdf|journal=Trakia Journal of Sciences|volume=3|pages=195-197|via=}}
3. ^{{cite book |title=The Chemical Formulary |date=1933 |publisher=David Van Nostrand Company Inc. |page=86 |url=https://archive.org/details/in.ernet.dli.2015.239029/page/n5}}

Synthesis

Uses

References

See also