Pararosaniline

Pararosaniline, Basic Red 9, or C.I. 42500 is an organic compound with the formula [(H2NC6H4)3C]Cl. It is a magenta solid with a variety of uses as a dye.[1] It is one of the four components of basic fuchsine. (The others are rosaniline, new fuchsine and magenta II.)[2] It is structurally related to other triarylmethane dyes called methyl violets including crystal violet, which feature methyl groups on nitrogen.

Pararosaniline
Names
IUPAC name
[4-[Bis(4-aminophenyl)methylidene]-1-cyclohexa-2,5-dienylidene]dianiline
Other names
Pararosaniline
p-rosaniline
C.I. 42500
Para magenta
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.106.992
KEGG
UNII
Properties
C19H17N3
Molar mass 323.83 g/mol
Appearance Green crystalline solid
Melting point 268 to 270 °C (514 to 518 °F; 541 to 543 K) decomposes
Slightly soluble
Hazards
Safety data sheet External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

It is prepared by the condensation of aniline and para-aminobenzaldehyde. Alternatively, it arises from the oxidation of 4,4'-bis(aminophenyl)methane in the presence of aniline.

Uses
  • It is used to dye polyacrylonitrile fibers.
  • Pararosaniline is used as a colorimetric test for aldehydes, in the Schiff test. It is the only basic fuchsine component suitable for making the aldehyde-fuchsine stain for pancreatic islet beta cells.[3]
  • It has use as an Antischistosomal GB 908634 (1962 to Parke Davis & Co).

References
  1. Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a27_179
  2. Horobin RW, Kiernan JA (2002) Conn's Biological Stains, 10th ed. Oxford: BIOS.
  3. Mowry, RW; Emmel, VM (1978). "Aldehyde fuchsin staining, direct or after oxidation: problems and remedies, with special reference to pancreatic B cells, pituitaries and elastic fibers". Stain Technology. 53: 141–154. doi:10.3109/10520297809111457.

Further reading
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