2-Thiophenecarboxylic acid

Chemical properties

The substance is a light yellow crystal powder. It dissolves in hot water, ethanol, and ether, and is only slightly soluble in chloroform.

The Uses of 2-Thiophenecarboxylic acid

2-Thenoic Acid, is a sulfur-containing heterocyclic compound, used in the synthesis of pharmaceutical and biologically active compounds. It is also shown to be utilized by presumptive Rhodococcus bacterium in soil, as a sole source of carbon.

Definition

ChEBI: Thiophene-2-carboxylic acid is a thiophenecarboxylic acid in which the carboxy group is located at position 2. It is a conjugate acid of a thiophene-2-carboxylate.

Production Methods

Thiophene 2-Carboxylic Acid, T2CA, is prepared via oxidation of 2-acetylthiophene using hypochlorite, because oxidation of alkylthiophenes leads to general breakdown of the thiophene ring.

What are the applications of Application

The sodium salt of 2-Thiophenecarboxylic acid(T2CA) is used to treat influenza (trophires). Other salts, e.g., the Li salt, have minor medicinal uses and the free acid is a mucolytic. A US Patent describes the use of the Na salt as a lubricating oil thickener. ?Suprofen, a nonsteroidal anti-inflammatory (NSAI), and tienilic acid (ticrynafen), a potent diuretic, were both very large prospective markets for T2CA or its acid chloride, but were almost completely withdrawn in the 1980s. Sanofi Aventis'NSAI tiaprofenic acid was comparatively successful in this market, but although it is still marketed it has subsequently been superceded by alternative products. The 5-nitro derivative of T2CA is used to produce nifurzide, an intestinal antibacterial. Pfizer's anti-inflammatory tenidap is a developing drug which uses the acid chloride of T2CA as the starting intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 3520, 1965 DOI: 10.1021/jo01021a055

Purification Methods

Crystallise the acid from water and dry it in a vacuum. The amide has m 181o(from H2O) and pK2 5 10.54(50% aqueous dioxane). [Beilstein 18 H 289, 18 I 438, 18 II 269, 18 III/IV 4011, 18/6 V 158.]