CI Basic Red 9
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Pararosaniline, pararosaniline free base, Basic Red 9, or C.I. 42500 is an
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
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 betwe ...
. It is the
free base In chemistry, a free base (freebase, free-base) is a term for the neutral form of an amine or other Lewis base. The term is used in the pharmaceutical industry in contrast to salt-based formulations like hydrochlorides. The amine is often an ...
form of pararosaniline hydrochloride, , a
magenta Magenta () is a purple-red color. On color wheels of the RGB color model, RGB (additive) and subtractive color, CMY (subtractive) color models, it is located precisely midway between blue and red. It is one of the four colors of ink used in colo ...
solid with a variety of uses as a
dye Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy Fantasy is a genre of speculative fiction that involves supernatural or Magic (supernatural), magical ele ...
. It is one of the four components of basic fuchsine. 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 pain ...
s (e.g.
crystal violet Crystal violet or gentian violet, also known as methyl violet 10B or hexamethyl pararosaniline chloride, is a triphenylmethane, triarylmethane dye used as a histological stain and in Gram staining, Gram's method of classifying bacteria. Crystal ...
) which feature methyl groups on nitrogen. It is prepared by the condensation of
aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
and . 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) is a synthetic, semicrystalline organic polymer resin, with the linear formula (CH2CHCN)n. Almost all PAN resins are copolymers with acrylonitrile as the main monomer. PAN is used to produce large variety of products in ...
fibers. *It is used to detect
sulfur dioxide Sulfur dioxide (IUPAC-recommended spelling) or sulphur dioxide (traditional Commonwealth English) is the chemical compound with the formula . It is a colorless gas with a pungent smell that is responsible for the odor of burnt matches. It is r ...
. *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.


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. It typically appears as an (off-)white solid powder. An analogue of TDA is the drug dapsone, for which the su ...
*
4,4'-Methylenedianiline 4,4′-Methylenedianiline (MDA) is an organic compound with the formula . 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. Synthesi ...
*
4,4'-Oxydianiline 4,4′-Oxydianiline (ODA) is an organic compound with the chemical formula, formula Oxygen, O(Carbon, C6Hydrogen, H4Nitrogen, NH2)2. It is an ether derivative of aniline. This colourless solid is a useful monomer and Cross-link, cross-linking agent ...
*
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 an ...


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 Hydrochlorides Carbocations