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Thiophene-2-carboxylic acid
Names
Other names
2-thenoic acid; tenoic acid; Rhinotrophyl
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.659 Edit this at Wikidata
EC Number
  • 208-423-4
KEGG
UNII
  • InChI=1S/C5H4O2S/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7)
    Key: QERYCTSHXKAMIS-UHFFFAOYSA-N
  • C1=CSC(=C1)C(=O)O
Properties
C5H4O2S
Molar mass 128.15 g·mol−1
Appearance white solid
Melting point 125–127 °C (257–261 °F; 398–400 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thiophene-2-carboxylic acid is an organic compound with the formula SC4H3CO2H. It is one of two monocarboxylic acids of thiophene, the other being thiophene-3-carboxylic acid.[1] Copper(I) thiophene-2-carboxylate is a catalyst for Ullmann coupling reactions.

Synthesis[edit]

It can be prepared by the oxidation of thiophene-2-carboxaldehyde or, more practically, 2-acetylthiophene.[2]

Applications and reactions[edit]

Suprofen, which is produced from thiophene-2-carboxylic acid, is the active ingredient in some eye drops.[2]

Upon treatment with LDA, thiophene-2-carboxylic acid undergoes double deprotonation to give the 5-lithio derivative, a precursor to many 5-substituted derivatives.[3]

Thiophene-2-carboxylic acid has been widely studied as a substrate in coupling reactions and olefinations.[4][5]

References[edit]

  1. ^ E. Campaigne, William M. LeSuer (1953). "3-Thenoic Acid". Organic Syntheses. 33: 94. doi:10.15227/orgsyn.033.0094.
  2. ^ a b Swanston, Jonathan (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 3527306730..
  3. ^ Knight, David W.; Nott, Andrew P. (1983). "Generation and Synthetic Utility of Dianions Derived from Thiophenecarboxylic Acids". Journal of the Chemical Society, Perkin Transactions 1: 791–4. doi:10.1039/p19830000791.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Gooßen, Lukas J.; Deng, Guojun; Levy, Laura M. (2006). "Synthesis of Biaryls via Catalytic Decarboxylative Coupling". Science. 313 (5787): 662–664. Bibcode:2006Sci...313..662G. doi:10.1126/science.1128684. PMID 16888137. S2CID 1781760.
  5. ^ Rakshit, Souvik; Grohmann, Christoph; Besset, Tatiana; Glorius, Frank (2011). "Rh(III)-Catalyzed Directed C−H Olefination Using an Oxidizing Directing Group: Mild, Efficient, and Versatile". Journal of the American Chemical Society. 133 (8): 2350–2353. doi:10.1021/ja109676d. PMID 21275421.
source: https://en.wikipedia.org/wiki/Thiophene-2-carboxylic_acid

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