Disodium 4,4′-dinitrostilbene-2,2′-disulfonate 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 (O₂NC₆H₃(SO₃Na)CH)₂. This salt is a common precursor to a variety of textile dyes 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 Aromatic sulfonation is an organic reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group in an electrophilic aromatic substitution. Aryl sulfonic acids are used as detergents, dye, and drugs. Stoichiometry a ...

4-nitrotoluene 4-Nitrotoluene or ''para''-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene. Synthesis and reactions Together with other isomers, 4-nitrotoluene is prepared by ...

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

sodium hypochlorite Sodium hypochlorite (commonly known in a dilute solution as bleach) is an Inorganic chemistry, inorganic chemical compound with the chemical formula, formula NaOCl (or NaClO), comprising a sodium cation () and a hypochlorite anion (or ). It may ...

yields the disodium

salt Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quantitie ...

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

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 ...

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 ...

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 ( he, אברהם יצחק גרין, 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, where he ...

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. ''Chemische Berichte'' (usually abbreviated as ''Ber.'' or ''Chem. Ber.'') was a German-language scientific journal of all disciplines of chemistry founded in 1868. It was one of the oldest scientific journals in chemistry, until it merged with ' ...

, year = 1898, volume = 31, issue = 1, pages = 1078–1080, doi = 10.1002/cber.189803101195, url = https://zenodo.org/record/1425898

References

Benzenesulfonates Azo compounds Stilbenoids Organic sodium salts