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
CAS Number	569-61-9^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
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	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

• Colour Index 3rd Edition Volume 4 (PDF), Bradford: Society of Dyers and Colourists, 1971, p. 4388, archived from the original (PDF) on 2011-07-19.
• Gessner, T.; Mayer, U. (2002), "Triarylmethane and Diarylmethane Dyes", Ullmann's Encyclopedia of Industrial Chemistry 6th Edition, Weinheim: Wiley-VCH, doi:10.1002/14356007.a27_179.