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Methyl violet 6B

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Methyl violet 6B
Methyl violet 6B
Names
IUPAC name 4--(4-methyliminocyclohexa-2,5-dien-1-ylidene)methyl]-N,N-dimethylaniline·hydrochloride
Other names
  • Gentian violet B,
  • Methylrosanilinium chloride,
  • Pentamethylparosanilinium chloride,
  • Basic Violet 3,
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.009.130 Edit this at Wikidata
EC Number
  • 610-776-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C24H27N3.ClH/c1-25-21-12-6-18(7-13-21)24(19-8-14-22(15-9-19)26(2)3)20-10-16-23(17-11-20)27(4)5;/h6-17H,1-5H3;1HKey: JFTBTTPUYRGXDG-UHFFFAOYSA-N
SMILES
  • CN=C1C=CC(=C(C2=CC=C(C=C2)N(C)C)C3=CC=C(C=C3)N(C)C)C=C1.Cl
Properties
Chemical formula C24H28N3Cl
Appearance Green to dark-green powder
Melting point 137 °C (279 °F; 410 K) decomposes
Solubility in water Soluble in water, ethanol, insoluble in xylene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound
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Methyl violet 6B (Pentamethylparosanilinium chloride, 4--(4-methyliminocyclohexa-2,5-dien-1-ylidene)methyl]-N,N-dimethylaniline·hydrochloride) is a violet triarylmethane dye from the group of cationic dyes and an essential component of C.I. Basic Violet 1 (trivial name methyl violet). The compound is sometimes equated with methyl violet in the literature.

Methyl violets are mixtures of tetramethyl (2B), pentamethyl (6B) and hexamethyl (10B) pararosanilins.

Synthesis

To produce methyl violet 6B, N,N-dimethylaniline is oxidized with atmospheric oxygen and copper sulfate as a catalyst, using phenol and large amounts of salt as a diluent. The central carbon atom of the dye is provided by the oxidation of a methyl group of N,N-dimethylaniline to formaldehyde. In this process, a reaction product is obtained that contains the tetra- to hexamethylated compounds in addition to the pentamethylated compound.

Synthesis of Methyl violet 6B
Synthesis of Methyl violet 6B

References

  1. ^ R. W. Sabnis (29 March 2010). Handbook of Biological Dyes and Stains: Synthesis and Industrial Applications. John Wiley and Sons. pp. 309–. ISBN 978-0-470-40753-0. Retrieved 27 June 2011.
  2. C. Bouasla, M. E. H. Samar, F, Ismail: Degradation of methyl violet 6B dye by the Fenton process. In: Desalination. 254.1–3, 2010, S. 35–41, doi:10.1016/j.desal.2009.12.017.
  3. K. Venkataraman (1952), The Chemistry of Synthetic Dyes, vol. II, New York, London: Academic Press, p. 719
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