Sulfanilic acid

Sulfanilic acid
Names
	Preferred IUPAC name 4-Aminobenzene-1-sulfonic acid[1]
	Other names 4-Aminobenzenesulfonic acid; p-Aminobenzenesulfonic acid; Sulfanilic acid (not retained[1])
Identifiers
CAS Number	121-57-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27500 ;
ECHA InfoCard	100.004.075
PubChem CID	8479;
UNII	434Z8C2635 ;
CompTox Dashboard (EPA)	DTXSID6024464 ;
	InChI InChI=1/C6H7NO3S/c7-5-; 1-3-6(4-2-5)11(8,9)10/h1-4H,; 7H2,(H,8,9,10)/f/h8H;
	SMILES OS(=O)(=O)c1ccc(N)cc1;
Properties
Chemical formula	C6H7NO3S
Molar mass	173.19
Density	1.485
Melting point	288 °C (550 °F; 561 K)
Solubility in water	12.51 g/L
Acidity (pKa)	3.23 (H2O)[2]
Related compounds
Related sulfonic acids	Benzenesulfonic acid; p-Toluenesulfonic acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Sulfanilic acid (4-aminobenzenesulfonic acid) is an organic compound with the formula H₃NC₆H₄SO₃. It is an off-white solid. It is a zwitterion, which explains its high melting point. It is a common building block in organic chemistry.[3]

Synthesis

Sulfanilic acid can be produced by sulfonation of aniline:[4]

Applications

As the compound readily forms diazo compounds, it is used to make dyes and sulfa drugs.[3] This property is also used for the quantitative analysis of nitrate and nitrite ions by diazonium coupling reaction with N-(1-Naphthyl)ethylenediamine, resulting in an azo dye, and the concentration of nitrate or nitrite ions were deduced from the color intensity of the resulting red solution by colorimetry.[5]

It is also used as a standard in combustion analysis and in the Pauly reaction.

Environmental aspects

Reflecting its wide use, sulfanilic acid is found in the leachates of landfills.[6] It is produced by reduction of some azo dyes.[7]

Derivatives

Methyl orange (azo coupling with dimethylaniline)
Acid orange 7 (azo coupling with 2-naphthol)[8]
Chrysoine resorcinol (azo coupling with resorcinol)

References

Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 789. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The name ‘sulfanilic acid’ is not retained.
Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–88. ISBN 978-1498754286.
"Sulphanilic acid". A Dictionary of Chemistry. Oxford University Press, 2000. Oxford Reference Online. Oxford University Press.
Siegfried Hauptmann: Organische Chemie, 2nd Edition, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, p. 511, ISBN 3-342-00280-8.
G. H. Jerffery; J. Bassett; J. Mendham; R. C. Denney (1989). "Colorimetry and Spectrophotometry". Vogel's Textbook of Quantitative Chemical Analysis, 5th Edition. Longman. p. 702. ISBN 0-582-44693-7.
Holm, John V.; Ruegge, Kirsten.; Bjerg, Poul L.; Christensen, Thomas H. (1995). "Occurrence and Distribution of Pharmaceutical Organic Compounds in the Groundwater Downgradient of a Landfill (Grindsted, Denmark)". Environmental Science & Technology. 29 (5): 1415–1420. doi:10.1021/es00005a039. PMID 22192041.
Nam, S. (2000). "Reduction of azo dyes with zero-valent iron". Water Research. 34 (6): 1837–1845. doi:10.1016/S0043-1354(99)00331-0.
Klaus Hunger; Peter Mischke; Wolfgang Rieper; Roderich Raue; Klaus Kunde; Aloys Engel (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245..

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[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 789. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The name ‘sulfanilic acid’ is not retained.

[CRC97-2] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–88. ISBN 978-1498754286.

[DOC-3] "Sulphanilic acid". A Dictionary of Chemistry. Oxford University Press, 2000. Oxford Reference Online. Oxford University Press.

[Hauptmann-4] Siegfried Hauptmann: Organische Chemie, 2nd Edition, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, p. 511, ISBN 3-342-00280-8.

[Vogel-5] G. H. Jerffery; J. Bassett; J. Mendham; R. C. Denney (1989). "Colorimetry and Spectrophotometry". Vogel's Textbook of Quantitative Chemical Analysis, 5th Edition. Longman. p. 702. ISBN 0-582-44693-7.

[6] Holm, John V.; Ruegge, Kirsten.; Bjerg, Poul L.; Christensen, Thomas H. (1995). "Occurrence and Distribution of Pharmaceutical Organic Compounds in the Groundwater Downgradient of a Landfill (Grindsted, Denmark)". Environmental Science & Technology. 29 (5): 1415–1420. doi:10.1021/es00005a039. PMID 22192041.

[7] Nam, S. (2000). "Reduction of azo dyes with zero-valent iron". Water Research. 34 (6): 1837–1845. doi:10.1016/S0043-1354(99)00331-0.

[Ullmann-8] Klaus Hunger; Peter Mischke; Wolfgang Rieper; Roderich Raue; Klaus Kunde; Aloys Engel (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245..