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
  • InChI=1S/C19H17N3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20H,21-22H2 ☒N
    Key: AFAIELJLZYUNPW-UHFFFAOYSA-N ☒N
  • InChI=1/C19H17N3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20H,21-22H2
    Key: AFAIELJLZYUNPW-UHFFFAOYAS
  • c1cc(ccc1C(=C2C=CC(=N)C=C2)c3ccc(cc3)N)N
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 (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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. J. B. Pate, J. P. Lodge, A. F. Wartburg (1962). "Effect of Pararosaniline in the Trace Determination of Sulfur Dioxide". Analytical Chemistry. 34 (12): 1660–1662. doi:10.1021/ac60192a001. ISSN 0003-2700. Retrieved 2023-03-03.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. 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 (3): 141–154. doi:10.3109/10520297809111457. PMID 83035.
  5. GB 908634, "Pharmaceutical compositions containing pararosaniline or derivatives thereof", published 1962-10-24, assigned to Parke, Davis & Co.

Further reading
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