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
CAS Number	3248-91-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:87671
ChEMBL	ChEMBL1979779
ChemSpider	17578
ECHA InfoCard	100.019.847
EC Number	221-831-7
PubChem CID	18611
UNII	A051F48W36 base
CompTox Dashboard (EPA)	DTXSID80879817
InChI InChI=1S/C22H23N3.ClH/c1-13-10-16(4-7-19(13)23)22(17-5-8-20(24)14(2)11-17)18-6-9-21(25)15(3)12-18;/h4-12,23H,24-25H2,1-3H3;1H Key: IPSIPYMEZZPCPY-UHFFFAOYSA-N
SMILES CC1=CC(=C(C2=CC(=C(C=C2)N)C)C3=CC(=C(C=C3)N)C)C=CC1=[NH2+].[Cl-]
Properties
Chemical formula	C22H24ClN3
Molar mass	365.91 g·mol^−1
Appearance	violet powder
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H315, H318, H319, H335, H350, H351, H373, H400, H410
GHS precautionary statements	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

• Fuchsine
• Pararosaniline

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.

External links

• New Fuchsin - StainsFile