Disodium 4,4'-dinitrostilbene-2,2'-disulfonate

Disodium 4,4'-dinitrostilbene-2,2'-disulfonate
Identifiers
CAS Number	3709-43-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	4651070;
ECHA InfoCard	100.020.956
PubChem CID	5713304;
UNII	4U494VHI4D ;
CompTox Dashboard (EPA)	DTXSID7027542 ;
	InChI InChI=1S/C14H10N2O10S2.2Na/c17-15(18)11-5-3-9(13(7-11)27(21,22)23)1-2-10-4-6-12(16(19)20)8-14(10)28(24,25)26;;/h1-8H,(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2/b2-1+;; Key: SDCDTWFAOKXZHD-SEPHDYHBSA-L;
	SMILES c1cc(c(cc1[N+](=O)[O-])S(=O)(=O)[O-])/C=C/c2ccc(cc2S(=O)(=O)[O-])[N+](=O)[O-].[Na+].[Na+];
Properties
Chemical formula	C14H8N2Na2O10S2
Molar mass	474.335
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Disodium 4,4′-dinitrostilbene-2,2′-disulfonate is an organic compound with the formula (O₂NC₆H₃(SO₃Na)CH)₂ This salt is a common precursor to a variety of textile dyes and optical brighteners

Preparation and reactions

The synthesis of disodium 4,4′-dinitrostilbene-2,2′-disulfonate begins with sulfonation of 4-nitrotoluene. This reaction affords 4-nitrotoluene-2-sulfonic acid. Oxidation of this species with sodium hypochlorite yields the disodium salt of 4,4′-dinitrostilbene-2,2′-disulfonic acid.[1] The product is useful as its reaction with aniline derivatives results in the formation of azo dyes. Commercially important dyes derived from this compound include Direct Red 76, Direct Brown 78, and Direct Orange 40.[2] Reduction gives 4,4′-diamino-2,2′-stilbenedisulfonic acid, which is a common optical brightener.

Structure of Direct Yellow 12, an azo dye produced from disodium 4,4′-dinitrostilbene-2,2′-disulfonate.

History

Arthur Green and André Wahl first reported the formation of disodium 4,4'-dinitrostilbene-2,2'-disulfonate using sodium hypochlorite.[3][4]

gollark: > yes that is when they typically are created.Future reminders were planned but deemed unworkable with current technology.

gollark: Then... adjectives?

gollark: Ah yes, thus adjectives.

gollark: <@!160279332454006795> It should say "you utter [thing]" too.

gollark: <@!160279332454006795> It's spelt equivalent.

References

Cumming, William M.; Hopper, I. Vance; Wheeler, T. Sherlock (1926). "Preparation 294.—Dinitro-Stilbene-Disulphonic Acid (Na salt)". Systematic Organic Chemistry: Modern Methods of Preparation and Estimation. New York: D. Van Nostrand Company. p. 314.
Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245.
Green, Arthur G.; Wahl, André R. (1897). "Ueber die Oxydation von Paranitrotoluolsulfosäure" [On the oxidation of para-nitrotoluenesulfonic acid]. Ber. Dtsch. Chem. Ges. (in German). 30 (3): 3097–3101. doi:10.1002/cber.189703003128.
Green, Arthur G.; Wahl, André R. (1898). "Ueber die Oxydation der Paranitrotoluolsulfosäure" [On the oxidation of para-nitrotoluenesulfonic acid]. Ber. Dtsch. Chem. Ges. (in German). 31 (1): 1078–1080. doi:10.1002/cber.189803101195.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Cumming, William M.; Hopper, I. Vance; Wheeler, T. Sherlock (1926). "Preparation 294.—Dinitro-Stilbene-Disulphonic Acid (Na salt)". Systematic Organic Chemistry: Modern Methods of Preparation and Estimation. New York: D. Van Nostrand Company. p. 314.

[Ullmann-2] Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245.

[3] Green, Arthur G.; Wahl, André R. (1897). "Ueber die Oxydation von Paranitrotoluolsulfosäure" [On the oxidation of para-nitrotoluenesulfonic acid]. Ber. Dtsch. Chem. Ges. (in German). 30 (3): 3097–3101. doi:10.1002/cber.189703003128.

[4] Green, Arthur G.; Wahl, André R. (1898). "Ueber die Oxydation der Paranitrotoluolsulfosäure" [On the oxidation of para-nitrotoluenesulfonic acid]. Ber. Dtsch. Chem. Ges. (in German). 31 (1): 1078–1080. doi:10.1002/cber.189803101195.