Fuchsine

Solid basic fuchsine

Basic fuchsine in aqueous solution

Names

IUPAC name

4-[(4-Aminophenyl)-(4-imino-1-cyclohexa-2,5-dienylidene)methyl]aniline hydrochloride

Identifiers

CAS Number

632-99-5^Y

3D model (Jmol)

CHEBI:87665^N

ChEMBL1979636^N

10468578^N

8053-09-6

8UUC89LHB2^Y

InChI=1S/C20H19N3.ClH/c1-13-12-16(6-11-19(13)23)20(14-2-7-17(21)8-3-14)15-4-9-18(22)10-5-15;/h2-12,21H,22-23H2,1H3;1H/b20-14-,21-17?;^N

Key: NIKFYOSELWJIOF-SVFFXJIWSA-N^N
InChI=1/C20H19N3.ClH/c1-13-12-16(6-11-19(13)23)20(14-2-7-17(21)8-3-14)15-4-9-18(22)10-5-15;/h2-12,21H,22-23H2,1H3;1H/b20-14-,21-17?;

Key: NIKFYOSELWJIOF-SVFFXJIWBQ

SMILES

[Cl-].[NH2+]=C\1/C=C\C(C=C/1)=C(\c2ccc(N)c(C)c2)c3ccc(N)cc3

Properties

Chemical formula

C₂₀H₁₉N₃·HCl

Molar mass

337.86 g/mol (hydrochloride)

Appearance

Dark green powder

Melting point

200 °C (392 °F; 473 K)

Solubility in water

2650 mg/L (25 °C (77 °F))

log P

2.920

Vapor pressure

7.49×10⁻¹⁰ mmHg (25 °C)

Henry's law
constant (k_H)

2.28×10⁻¹⁵ atm⋅m³/mole (25 °C)

Atmospheric OH rate constant

4.75×10⁻¹⁰ cm³/molecule⋅sec (25 °C)

Hazards

Main hazards

Ingestion, inhalation, skin and eye contact, combustible at high temperature, slightly explosive around open flames and sparks.

NFPA 704

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

Fuchsine (sometimes spelled fuchsin) or rosaniline hydrochloride is a magenta dye with chemical formula C₂₀H₁₉N₃·HCl. There are other similar chemical formulations of products sold as fuchsine, and several dozen other synonyms of this molecule.

It becomes magenta when dissolved in water; as a solid, it forms dark green crystals. As well as dying textiles, fuchsine is used to stain bacteria and sometimes as a disinfectant. In the literature of biological stains the name of this dye is frequently misspelled, with omission of the terminal -e, which indicates an amine. American and English dictionaries (Webster's, Oxford, Chambers, etc.) give the correct spelling, which is also used in the literature of industrial dyeing. It is well established that production of fuchsine results in development of bladder cancers by production workers. Production of magenta is listed as a circumstance known to result in cancer.

Fuchsine was first prepared by August Wilhelm von Hofmann from aniline and carbon tetrachloride in 1858.François-Emmanuel Verguin discovered the substance independently of Hofmann the same year and patented it. Fuchsine was named by its original manufacturer Renard frères et Franc, is usually cited with one of two etymologies: from the color of the flowers of the plant genus Fuchsia, named in honor of botanist Leonhart Fuchs, or as the German translation Fuchs of the French name Renard, which means fox. An 1861 article in Répertoire de Pharmacie said that the name was chosen for both reasons.

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