Disodium 4,4′-dinitrostilbene-2,2′-disulfonate 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 (O₂NC₆H₃(SO₃Na)CH)₂. This salt is a common precursor to a variety of textile

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 ...

s and

optical brightener Optical brighteners, optical brightening agents (OBAs), fluorescent brightening agents (FBAs), or fluorescent whitening agents (FWAs), are chemical compounds that absorb light in the ultraviolet and violet region (usually 340-370 nm) of the ...

Preparation and reactions

The synthesis of disodium 4,4′-dinitrostilbene-2,2′-disulfonate begins with

sulfonation In organic chemistry, aromatic sulfonation is a reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid () group. Together with nitration and chlorination, aromatic sulfonation is a widely used electrophilic aromatic substi ...

of 4-nitrotoluene. This reaction affords 4-nitrotoluene-2-sulfonic acid. Oxidation of this species with

sodium hypochlorite Sodium hypochlorite is an alkaline inorganic chemical compound with the formula (also written as NaClO). It is commonly known in a dilute aqueous solution as bleach or chlorine bleach. It is the sodium salt of hypochlorous acid, consisting of ...

yields the disodium

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

of 4,4′-dinitrostilbene-2,2′-disulfonic acid. The product is useful as its reaction with

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 ...

derivatives results in the formation of

azo dye Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C−N=N−C l ...

s. Commercially important dyes derived from this compound include Direct Red 76, Direct Brown 78, and Direct Orange 40. Reduction gives 4,4′-diamino-2,2′-stilbenedisulfonic acid, which is a common

History

Arthur Green Arthur Green (, born March 21, 1941) is an American scholar of Jewish mysticism and Neo-Hasidic theologian. He was a founding dean of the non-denominational rabbinical program at Hebrew College in Boston. He describes himself as an American Jew ...

and André Wahl first reported the formation of disodium 4,4'-dinitrostilbene-2,2'-disulfonate using

.{{cite journal, title = Ueber die Oxydation der Paranitrotoluolsulfosäure, language = German, trans-title = On the oxidation of ''para''-nitrotoluenesulfonic acid, first1 = Arthur G., last1 = Green, authorlink1 = Arthur George Green, first2 = André R., last2 = Wahl, journal = Ber. Dtsch. Chem. Ges., year = 1898, volume = 31, issue = 1, pages = 1078–1080, doi = 10.1002/cber.189803101195, url = https://zenodo.org/record/1425898

References

Benzenesulfonates Nitrobenzene derivatives Stilbenoids Organic sodium salts