Pararosaniline, Basic Red 9, or
C.I. 42500 is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...
2NC6H4)3C">H2NC6H4)3Cl. It is a
magenta
Magenta () is a color that is variously defined as pinkish- purplish-red, reddish-purplish-pink or mauvish-crimson. On color wheels of the RGB (additive) and CMY (subtractive) color models, it is located exactly midway between red and blue. I ...
solid with a variety of uses as a
dye
A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution an ...
. It is one of the four components of basic
fuchsine
Fuchsine (sometimes spelled fuchsin) or rosaniline hydrochloride is a magenta dye with chemical formula C20H19N3·HCl. . (The others are
rosaniline
Fuchsine (sometimes spelled fuchsin) or rosaniline hydrochloride is a magenta dye with chemical formula C20H19N3·HCl. ,
new fuchsine
New fuchsine is an organic compound with the formula H2N(CH3)C6H3)3Cl. It is a green-colored solid that is used as a dye of the triarylmethane class. It is one of the four components of basic fuchsine, and one of the two that are available as ...
and magenta II.) It is structurally related to other triarylmethane dyes called
methyl violet
Methyl violet is a family of organic compounds that are mainly used as dyes. Depending on the number of attached methyl groups, the color of the dye can be altered. Its main use is as a purple dye for textiles and to give deep violet colors in p ...
s including
crystal violet
Crystal violet or gentian violet, also known as methyl violet 10B or hexamethyl pararosaniline chloride, is a triarylmethane dye used as a histological stain and in Gram's method of classifying bacteria. Crystal violet has antibacterial, antif ...
, which feature methyl groups on nitrogen.
It is prepared by the condensation of
aniline
Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine
In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...
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
Polyacrylonitrile (PAN), also known as polyvinyl cyanide and Creslan 61, is a synthetic, semicrystalline organic polymer resin, with the linear formula (C3H3N)n. Though it is thermoplastic, it does not melt under normal conditions. It degrades bef ...
fibers.
*Pararosaniline is used as a colorimetric test for aldehydes, in the
Schiff test
:
The Schiff test is an early organic chemistry named reaction developed by Hugo Schiff, and is a relatively general chemical test for detection of many organic aldehydes that has also found use in the staining of biological tissues. The Schiff ...
. 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
Schistosomiasis, also known as snail fever, bilharzia, and Katayama fever, is a disease caused by parasitic flatworms called schistosomes. The urinary tract or the intestines may be infected. Symptoms include abdominal pain, diarrhea, bloody ...
.
Related compounds
*
4,4'-Thiodianiline
4,4′-Thiodianiline (TDA) is the organosulfur compound with the formula (H2NC6H4)2S. It is classified as a diamine and a thioether. A colorless solid, it is used as a precursor to dyes. An analogue of TDA is dapsone.
Synthesis
Sulfur is boi ...
*
4,4'-Methylenedianiline
4,4′-Methylenedianiline (MDA) is an organic compound with the formula CH2(C6H4NH2)2. It is a colorless solid, although commercial samples can appear yellow or brown. It is produced on an industrial scale, mainly as a precursor to polyurethanes. ...
*
4,4'-Oxydianiline
4,4′-Oxydianiline (ODA) is an organic compound with the formula O( C6 H4 NH2)2. It is an ether derivative of aniline. This colourless solid is a useful monomer and cross-linking agent for polymers, especially the polyimides, such as Kapton.
Us ...
*
Dapsone
Dapsone, also known as 4,4'-sulfonyldianiline (SDA) or diaminodiphenyl sulfone (DDS), is an antibiotic commonly used in combination with rifampicin and clofazimine for the treatment of leprosy. It is a second-line medication for the treatment a ...
References
Further reading
*.
*{{citation , last1=Gessner , first1=T. , last2=Mayer , first2=U. , year=2002 , contribution= Triarylmethane and Diarylmethane Dyes , title= Ullmann's Encyclopedia of Industrial Chemistry 6th Edition , publisher=Wiley-VCH , place=Weinheim , doi=10.1002/14356007.a27_179 .
Triarylmethane dyes
IARC Group 2B carcinogens
Anilines
Chlorides