Triarylmethane dye

Triarylmethane dyes are synthetic organic compounds containing triphenylmethane backbones. As dyes, these compounds are
intensely colored. They are produced industrially as dyes.[1]

Contents
Families
Methyl violet dyes
Fuchsine dyes
Phenol dyes
Malachite green dyes
Victoria blue dyes
Bridged arenes
Synthesis
Applications
References

Families
Triarylmethane dyes can be grouped into families according to the nature of the substituents on the aryl groups. In some cases, the
anions associated with the cationic dyes (say crystal violet) vary even though the name of the dye does not. Often it is shown as
chloride.

Methyl violet dyes

Methyl violet dyes have dimethylamino groups at thep-positions of two aryl groups.

Methyl violet dyes

Methyl violet 2B Methyl violet 6B Methyl violet 10B

Fuchsine dyes
Fuchsine dyes have primary or secondary amines (NH
2 or NHMe) functional groups at thep-positions of each aryl group.

Fuchsine dyes
 Pararosaniline Fuchsine (hydrochloride salt) New fuchsine (As chloride)

Fuchsine acid

Phenol dyes
Phenol dyes have hydroxyl groups at thep positions of at least two aryl groups.

Phenol dyes

Phenolphthalein Phenol red Chlorophenol red

Cresol red Bromocresol purple Bromocresol green

Malachite green dyes
Malachite green dyes are related to the methyl violet dyes, except that they contain one phenyl (C
6H5) group.

Malachite green dyes

Malachite green Brilliant green (dye) Brilliant Blue FCF, a common food
colorant.

Victoria blue dyes

Victoria blue dyes are related to the methyl violet dyes, except they contain one naphthylamino group. Variation is found is
dimethylamine vs diethylamino substituents on the phenyl rings and variations of the secondary amine on the naphthyl group.

Victoria blue dyes

Victoria Blue B Victoria Blue FBR Victoria blue BO

Victoria Blue FGA Victoria blue 4 R Victoria blue R

Bridged arenes
Where two of the aryl groups are bridged by a heteroatom, these triarylmethane compounds may be further categorized into acridines
(nitrogen-bridged), xanthenes (oxygen-bridged), andthioxanthenes (sulfur-bridged).

Synthesis
The amine-containing dyes are often prepared fromMischler's ketone or its diethylamino analogue.In this way, the third aryl group is
readily differentiated. The Friedel–Crafts alkylationreaction is a popular method to prepare many of the phenolic derivatives:

Thymolphthalein

Applications
as indicators.[1]
In addition to their dominant use as dyes, many of these dyes react reversibly with acid and base, and thus serve pH

Bromocresol Green

References
1. Gessner, Thomas; Mayer, Udo (2000), "Triarylmethane and Diarylmethane Dyes",Ullmann's Encyclopedia of
Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a27_179(https://doi.org/10.1002/14356007.a27
_179)

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