New fuchsine

New fuchsine is an organic compound with the formula [(H2N(CH3)C6H3)3C]Cl. It is a green-colored solid that is used as a dye of the triarylmethane class. It is one of the four components of basic fuchsine, and one of the two that are available as single dyes.[1] The other is pararosaniline. It is prepared by condensation of ortho-toluidine with formaldehyde. This process initially gives the benzhydrol 4,4'-bis(dimethylamino)benzhydrol, which is further condensed to give the leuco (colorless) tertiary alcohol [(H2N(CH3)C6H3)3COH, which is oxidized in acid to give the dye.[2]

New fuchsine
Names
Other names
New fuchsin; Magenta III; Basic Violet 2; C.I. 42520
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.019.847
EC Number
  • 221-831-7
UNII
Properties
C22H24ClN3
Molar mass 365.91 g·mol−1
Appearance violet powder
Hazards
GHS pictograms
GHS Signal word Danger
H315, H318, H319, H335, H350, H351, H373, H400, H410
P201, P202, P260, P261, P264, P271, P273, P280, P281, P302+352, P304+340, P305+351+338, P308+313, P310, P312, P314, P321, P332+313, P337+313, P362, P391, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Use as dye and stain

New fuchsine is used to dye polyacrylonitrile, paper, and leather. In biology, it can be used for staining acid-fast organisms, e.g. by Ziehl-Neelsen stain, and for making Schiff's reagent. As a primary amine, the dye can be diazotized in the laboratory, and the resulting diazonium salt used as a trapping agent in enzyme histochemistry.[3]

Etymology

The name fuchsine recognizes Leonhart Fuchs.

See also

References

  1. Horobin RW, Kiernan JA (2002) Conn's Biological Stains, 10th ed. Oxford: BIOS.
  2. Thetford, Dean; Updated By Staff (2013). "Triphenylmethane and Related Dyes". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2018091620080520.a01.pub2. ISBN 978-0471238966.
  3. Lojda Z, Gossrau R, Schiebler TH (1979) Enzyme Histochemistry. A Laboratory Manual. Berlin: Springer-Verlag.
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