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Pararosaniline

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(Redirected from CI Basic Red 9)
Pararosaniline
Names
IUPAC name -1-cyclohexa-2,5-dienylidene]dianiline
Other names Pararosaniline
p-rosaniline
C.I. 42500
Para magenta
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.106.992 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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,21-22H2Key: AFAIELJLZYUNPW-UHFFFAOYSA-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,21-22H2Key: AFAIELJLZYUNPW-UHFFFAOYAS
SMILES
  • c1cc(ccc1C(=C2C=CC(=N)C=C2)c3ccc(cc3)N)N
Properties
Chemical formula 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
Solubility in water 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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.
  • It is used to detect sulfur dioxide.
  • 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.
  • It has use as an Antischistosomal.

Related compounds

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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