Pararosaniline

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
CAS Number	479-73-2^Y 569-61-9 (HCl)^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:87663^N
ChemSpider	10819^N
ECHA InfoCard	100.106.992
KEGG	C19210^Y
PubChem CID	11293
UNII	20N4C0M8NM^Y 444C2M8JKN (HCl)^Y
CompTox Dashboard (EPA)	DTXSID5043845
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,21-22H2^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
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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

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.

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.^[3]
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.^[4]
It has use as an Antischistosomal. ^[5]

Related compounds

References

^ 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
^ Horobin RW, Kiernan JA (2002) Conn's Biological Stains, 10th ed. Oxford: BIOS.
^ 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)
^ 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.
^ GB 908634, "Pharmaceutical compositions containing pararosaniline or derivatives thereof", published 1962-10-24, assigned to Parke, Davis & Co.