Bismarck brown Y

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Bismarck brown Y
BismarckBrownNeutral.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • 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+ X mark.svgN
    Key: BDFZFGDTHFGWRQ-OGGGYYITSA-N X mark.svgN
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 by German chemist Carl Alexander von Martius. It is used in histology for staining tissues. [2]

Contents

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.

Related Research Articles

Dye Soluble chemical substance or natural material which can impart color to other materials

A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution, and may require a mordant to improve the fastness of the dye on the fiber.

Aniline Chemical compound

Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds.

Nitrous acid Chemical compound

Nitrous acid is a weak and monoprotic acid known only in solution, in the gas phase and in the form of nitrite salts. Nitrous acid is used to make diazonium salts from amines. The resulting diazonium salts are reagents in azo coupling reactions to give azo dyes.

Staining Technique used to enhance visual contrast of specimens observed under a microscope

Staining is a technique used to enhance contrast in samples, generally at the microscopic level. Stains and dyes are frequently used in histology and in the medical fields of histopathology, hematology, and cytopathology that focus on the study and diagnoses of disease at a microscopic level. Stains may be used to define biological tissues, cell populations, or organelles within individual cells.

Congo red Chemical compound

Congo red is an organic compound, the sodium salt of 3,3′-([1,1′-biphenyl]-4,4′-diyl)bis(4-aminonaphthalene-1-sulfonic acid). It is an azo dye. Congo red is water-soluble, yielding a red colloidal solution; its solubility is greater in organic solvents. However, the use of Congo red has long been abandoned, primarily because of its carcinogenic properties.

Azo compound Class of organic compounds

Azo compounds are compounds bearing the functional group diazenyl R−N=N−R′, in which R and R′ can be either aryl or alkyl.

The diazogroup is an organic moiety consisting of two linked nitrogen atoms (azo) at the terminal position. Overall charge neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds or diazoalkanes and are described by the general structural formula R2C=N+=N. The simplest example of a diazo compound is diazomethane, CH2N2. Diazo compounds (R2C=N2) should not be confused with azo compounds of the type R-N=N-R or with diazonium compounds of the type R-N2+.

Safranin Chemical compound

Safranin is a biological stain used in histology and cytology. Safranin is used as a counterstain in some staining protocols, colouring cell nuclei red. This is the classic counterstain in both Gram stains and endospore staining. It can also be used for the detection of cartilage, mucin and mast cell granules.

Acid dye

Acid dyes are anionic, soluble in water and are essentially applied from acidic bath. These dyes possess acidic groups, such as SO3H and COOH and are applied on wool, silk and nylon when ionic bond is established between protonated –NH2 group of fibre and acid group of dye. Overall wash fastness is poor although lightfastness is quite good. As dye and fibre contain opposite electrical nature, strike rate and uptake of acid dye on these fibres is faster; electrolyte at higher concentration is added to retard dye uptake and to form levelled shades. Acid generates cation on fibre and temperature helps to substitute negative part of acid with anionic dye molecules.

Azo dye Class of organic compounds used as dye

Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl. They are a commercially important family of azo compounds, i.e. compounds containing the linkage C-N=N-C. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related to azo dyes are azo pigments, which are insoluble in water and other solvents.

Diazonium compound Diazonium salts of formula R-N≡N+

Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group R−N+2X where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halogen.

An azo coupling is an organic reaction between a diazonium compound and another aromatic compound that produces an azo compound. In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile and the activated arene is a nucleophile. In most cases, including the examples below, the diazonium compound is also aromatic.

Trypan blue is an azo dye. It is a direct dye for cotton textiles. In biosciences, it is used as a vital stain to selectively colour dead tissues or cells blue.

Solvent Black 3 is an azo dye. It is nonfluorescent, relatively thermostable lysochrome diazo dye used for staining of neutral triglycerides and lipids on frozen sections and some lipoproteins on paraffin sections. It has the appearance of a dark brown to black powder with maximum absorption at 596–605 nm and melting point 120–124 °C. It stains blue-black.

Papanicolaou stain Histological staining method

Papanicolaou stain is a multichromatic (multicolored) cytological staining technique developed by George Papanicolaou in 1942. The Papanicolaou stain is one of the most widely used stains in cytology, where it is used to aid pathologists in making a diagnosis. Although most notable for its use in the detection of cervical cancer in the Pap test or Pap smear, it is also used to stain non-gynecological specimen preparations from a variety of bodily secretions and from small needle biopsies of organs and tissues. Papanicolaou published three formulations of this stain in 1942, 1954, and 1960.

The formazans are compounds of the general formula [R-N=N-C(R')=N-NH-R"], formally derivatives of formazan [H2NN=CHN=NH], unknown in free form.

Sulfanilic acid Chemical compound

Sulfanilic acid (4-aminobenzenesulfonic acid) is an organic compound with the formula H3NC6H4SO3. It is an off-white solid. It is a zwitterion, which explains its high melting point. It is a common building block in organic chemistry.

Benzenediazonium tetrafluoroborate Organic compound containing an –N≡N+ function

Benzenediazonium tetrafluoroborate is an organic compound with the formula [C6H5N2]BF4. It is a salt of a diazonium cation and tetrafluoroborate. It exists as a colourless solid that is soluble in polar solvents. It is the parent member of the aryldiazonium compounds, which are widely used in organic chemistry.

Azo violet Chemical compound

Azo violet (4-(4-nitrophenylazo)resorcinol) (or p-nitrobenzeneazoresorcinol) is an azo compound with the chemical formula C12H9N3O4. It is used commercially as a violet dye and experimentally as a pH indicator, appearing yellow below pH 11, and violet above pH 13. It also turns deep blue in the presence of magnesium salt in a slightly alkaline, or basic, environment. Azo violet may also be used to test for the presence of ammonium ions. The color of ammonium chloride or ammonium hydroxide solution will vary depending upon the concentration of azo violet used.

<i>N</i>-(1-Naphthyl)ethylenediamine Chemical compound

N-(1-Naphthyl)ethylenediamine is an organic compound. It is commercially available as part of Griess reagents, which find application in quantitative inorganic analysis of nitrates, nitrite and sulfonamide in blood, using the Griess test.

References

  1. 1 2 3 Lillie, Ralph Dougall (1977). H. J. Conn's Biological stains (9th ed.). Baltimore: Williams & Wilkins. pp. 692p.
  2. 1 2 Booth, Gerald (2000). "Dyes, General Survey". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_073. ISBN   3527306730.
  3. Tomov, Nikola; Dimitrov, Nikolay (2017). "Modified Bismarck brown staining for demonstration of soft tissue mast cells" (PDF). Trakia Journal of Sciences. 15 (3): 195–197. doi: 10.15547/tjs.2017.03.001 .
  4. The Chemical Formulary. David Van Nostrand Company Inc. 1933. p.  86.