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Crystal violet

Crystal violet
Kekulé, skeletal formula of a crystal violet minor tautomer
Ball-and-stick model of crystal violet as a chloride salt
Names
IUPAC name
Tris(4-(dimethylamino)phenyl)methylium chloride
Other names
  • Aniline violet
  • Basic violet 3
  • Baszol Violet 57L
  • Brilliant Violet 58
  • Hexamethyl-p-rosaniline chloride
  • Methylrosanilide chloride
  • Methyl Violet 10B
  • Methyl Violet 10BNS
  • Pyoktanin
Identifiers
548-62-9 YesY
1733-13-7 (base) N
3D model (Jmol) Interactive image
Interactive image
3580948
ChEBI CHEBI:41688 N
ChEMBL ChEMBL64894 YesY
ChemSpider 10588 YesY
DrugBank DB00406 N
ECHA InfoCard 100.034.892
EC Number 208-953-6
KEGG D01046 YesY
MeSH Gentian+violet
PubChem 11057
CID 68050 from PubChem (base)
RTECS number BO9000000
UNII J4Z741D6O5 YesY
B4JIJ2C6AT (base) N
UN number 3077
Properties
C25H30ClN3
Molar mass 407.99 g·mol−1
Melting point 205 °C (401 °F; 478 K)
Pharmacology
D01AE02 (WHO) G01AX09 (WHO)
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H302, H318, H351, H410
P273, P280, P305+351+338, P501
Harmful Xn Dangerous for the Environment (Nature) N
R-phrases R22, R40, R41, R50/53
S-phrases (S2), S26, S36/37/39, S46, S60, S61
Lethal dose or concentration (LD, LC):
LD50 (median dose)
1.2 g/kg (oral, mice)

1.0 g/kg (oral, rats)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

1.0 g/kg (oral, rats)

Crystal violet or gentian violet (also known as methyl violet 10B or hexamethyl pararosaniline chloride) is a triarylmethane dye used as a histological stain and in Gram's method of classifying bacteria. Crystal violet has antibacterial, antifungal, and anthelmintic properties and was formerly important as a topical antiseptic. The medical use of the dye has been largely superseded by more modern drugs, although it is still listed by the World Health Organization.

The name "gentian violet" was originally used for a mixture of methyl pararosaniline dyes (methyl violet), but is now often considered a synonym for crystal violet. The name refers to its colour, being like that of the petals of a gentian flower; it is not made from gentians or from violets.

A number of possible routes can be used to prepare crystal violet. The original procedure developed by the German chemists Kern and Caro involved the reaction of dimethylaniline with phosgene to give 4,4′-bis(dimethylamino)benzophenone (Michler's ketone) as an intermediate. This was then reacted with additional dimethylaniline in the presence of phosphorus oxychloride and hydrochloric acid.

The dye can also be prepared by the condensation of formaldehyde and dimethylaniline to give a leuco dye:

Second, this colourless compound is oxidized to the coloured cationic form: (A typical oxidizing agent is manganese dioxide).


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