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 Y
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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H315, H318, H319, H335, H350, H351, H373, H410
Precautionary statements	P201, P202, P260, P261, P264, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P332+P313, P337+P313, P362, P391, P403+P233, 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.^{[citation needed]} 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