Bismark brown

Solubility Soluble in water, methyl cellosolve, ethylene glycol slightly soluble in ethanol insoluble in acetone, benzene, carbon tetrachloride, xylene 

CA Index Name 1,3-Benzenediatnine, 4,4 -[ 1,3-pheny-lenebis(2,l-diazenediyl)]bis-, hydrochloride (1 2) 

Merck Index Number 1253 Chemical/Dye Class Azo Molecular Formula C18H20CI2N8 Molecular Weight 419.31 

Physical Form Blackish-brown or red-brown powder 

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Nitro-l-diazo-2-naphthol-4-sulfonic acid prefers the 2-position in spite of the nitro group, and increasing alkalinity favors ortho coupling with diazophenols. 1-Naphthalenesulfamic acid [24344-19-2] (ArNHSO H) and N-nitro-1-naphthylamine [4323-69-7] (ArNHNO ) couple exclusively in the para position. The substitution of resorcinol [108-46-3] and y -phenylenediamine [108-45-2] is compHcated and has been discussed (29,30). The first azo dyes from aniline, eg. Aniline Yellow [60-09-3] (19) (Cl Solvent Yellow 1 Cl 11000) were manufactured in 1861 and Bismark Brown [10114-58-6] (20) (Cl Basic Brown 1 Cl 21000) appeared in 1863. The reaction is as follows ... 

Two important browns, other than benzidine derivatives, are of azo chemical composition. Direct Brown 30 [6222-60-2] (82) (Cl 17630) is produced by coupling Primuline [30133-37-2] (Cl 49000) to N-phenylgamma acid under alkaline conditions. Direct Brown 44 [6252-62-6] (Cl 35005-35010) is produced by coupling two moles of sulfanilic acid to Bismark Brown [10114-58-6] (Basic Brown 1) (Cl 21000) forming a heterogeneous product with a significant component (83). 

Bismarck Brown.—The dis-azo compound obtained meta-diamino benzene dis-azo benzene meta-di-amino benzene is a dye known as Bismark brown, though the dye is probably a mixture of the dis-azo compound and tri-amino azo benzene. With the exception of aniline yellow or amino azo benzene it was the first azo dye to be made. It was first prepared by Martins in 1864, and first made as a dye in 1866. 

Basic azo-dyes (chrysoi dine, Bismark brown) are dyed like all colour-bases on vegetable fibres prepared with tannic acid. Their principal application is in cotton-dyeing. 

Triamidoazobenzene is formed along with other azo-compounds, on treating metaphenylenediamine with nitrous acid. Its hydrochloride forms the principal constituent of the dyestuffs known under the above names. (A more recent view is that Bismark brown consists partly at least of a compound of the formula... 

With the exception of chrysoi dine, Bismark brown is the only basic azo-dyestuff in practical use. It is used in dyeing cotton and leather. 

Metaphenylenediamine may also be used, but the products are not so fast to light. Triamidoazobenzenes (Bismark brown) and Chrysoidine give soluble indulines on heating with paraphenylenediamine. 

SCHEME 5. The first azo dyes, and modem formula for Bismark brown (15a)... 

Results from our investigation on numerous (1, 2, 3) dyes,are given in our previous papers ruby s, Bismark brown, water blue, basic fuchsin, eosin bluish, eosin water-soluble, methyl red,crystal violet, alisarin yellow GG, diamant fuchsin, malachite green, etc. 

In the B type of dyes, which includes water blue, basic fuchsin, eosin bluish, eosin water-soluble and Bismark brown, the I-V characteristics with equal electrodes are also symmetric, but do not pass through the beginning of the coordinate system (Fig. lb). Here the current begins at a certain voltage different from zero, which in the different dyes varies from 50 to 300 mV. 

Synonyms [8-[(4-Amino-3-nitrophenyl) azo]-7-hydroxy-2-naphthyl] trimethylammonium chloride 8-[(4-Amino-3-nitrophenyl) azo]-7-hydroxy-N,N,N-trimethyl-2-naphthalenaminium chloride Cl 12251 2-Naphthalenaminium, 8-[(4-amino-3-nitrophenyl) azo]-7-hydroxy-N,N,N-trimethyl-, chloride Empirical C19H20N5O3 Cl Uses Colorant in hair dyes Basic brown 4, dihydrochloride CAS 5421-66-9 EINECS/ELINCS 226-541-4 Synonyms Basic brown 4 1,3-Benzenediamine, 4,4 -((4-methyl-1,3-phenylene) bis (azo)) bis (6-methyl)-, dihydrochloride Bismark brown R Cl 21010 4,4 -[(4-Methyl-1,3-phenylene) bis (azo)] bis [6-methyl-1,3-benzenediamine]... 

Bismarck brown Y. See Basic brown 1 Bismark brown R. See Basic brown 4, dihydrochloride... 

Basic Brown 1 (Bismark Brown) is an amino-containing dye that is readily proto-nated under the pH 2 to 5 conditions of dyeing ... 

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