Tobias acid

Tobias acid (2-amino-1-naphthalenesulfonic acid) is an organic compound with the formula C10H6(SO3H)(NH2). It is named after the German chemist Georg Tobias.[1] It is one of several aminonaphthalenesulfonic acids, which are derivatives of naphthalene containing both amine and sulfonic acid functional groups. It is a white solid, although commercial samples can appear otherwise.[2] It is used in the synthesis of azo dyes such as C.I. Acid Yellow 19 and C.I. Pigment Red 49. It is prepared via the Bucherer reaction of 2-hydroxynaphthalene-1-sulfonic acid with ammonia and ammonium sulfite.[3]

Tobias acid
Names
Preferred IUPAC name
2-Aminonaphthalene-1-sulfonic acid
Other names
2-Naphthylamine-1-sulfonic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.211
EC Number
  • 201-331-5
UNII
  • InChI=1S/C10H9NO3S/c11-9-6-5-7-3-1-2-4-8(7)10(9)15(12,13)14/h1-6H,11H2,(H,12,13,14)
    Key: GWIAAIUASRVOIA-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=CC(=C2S(=O)(=O)O)N
Properties
C10H9NO3S
Molar mass 223.25 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Tobias, Georg (January 1890). "Zur Anwendung der Sandmeyer' schen Reaction auf Diazosulfosäuren und über die Zersetzung dieser Verbindungen bei Gegenwart von Kupfer oder Kupferoxydul" [On the application of Sandmeyer's reaction to diazosulfonic acids and the decomposition of these compounds in the presence of copper or copper oxide]. Berichte der Deutschen Chemischen Gesellschaft (in German). 23 (1): 1628–1634. doi:10.1002/cber.189002301270.
  2. CID 6670 from PubChem
  3. Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_009.


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