5503-74-2

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Borono-2-thiophenecarboxylic acid is used as a building block for the synthesis of various pharmaceuticals due to its unique structural features and reactivity, contributing to the development of new drugs with improved therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Borono-2-thiophenecarboxylic acid is utilized as a versatile reagent, enabling the creation of a wide range of organic compounds with diverse applications.
Used in Study of Carbohydrate-Protein Interactions:
3-Borono-2-thiophenecarboxylic acid is employed as a reagent in the study of carbohydrate-protein interactions, particularly due to its ability to form complexes with diol molecules, which aids in understanding the underlying mechanisms of these interactions.
Used in Anti-Inflammatory Research:
3-Borono-2-thiophenecarboxylic acid has been investigated for its potential as an anti-inflammatory agent, with research focusing on its ability to modulate inflammatory processes and provide therapeutic benefits in conditions characterized by inflammation.
Used in Cancer Treatment Research:
In the field of oncology, 3-Borono-2-thiophenecarboxylic acid is being explored as a possible treatment for certain types of cancer, leveraging its unique chemical properties to target cancer cells and potentially contribute to cancer therapy.

Downstream Products

• 1103535-39-2 3-(4-bromo-3-methoxyphenyl)thiophene-2-carboxylic acid 

Relevant academic research and scientific papers

On the directing effect of boronate groups in the lithiation of boronated thiophenes

An investigation of thiophene boronates has revealed the usefulness of a metalation reaction in the synthesis of various lithiated thiophene boronates, which were further converted to functionalized thiopheneboronic derivatives. The lithiation of 2- and 3-thienylboronic N-butyldiethanolamine (BDEA) esters with lithium diisopropylamide and lithium 2,2,6,6-tetramethylpiperidide showed that both boronated thiophenes were readily deprotonated. In the latter case, lithiation at the 2-position adjacent both to sulfur and the borocanyl group is thermodynamically favoured due to the significant stabilizing effect of the borocanyl group. Further derivatization with a range of electrophiles followed by hydrolysis afforded various 2-substituted 3-thiopheneboronic acids. Lithiation of the corresponding thiopheneboronic "ate" complexes of the type [ThB(OR)3]Li revealed that the 2-thienyl derivatives could not be effectively deprotonated, whereas the "ate" complex, [3-ThB(OEt)3]Li, was selectively lithiated with nBuLi at C-2. This points to a directing effect of the anionic boronate moiety. The resulting bimetallic species, [(2-Li-3-Th)B(OEt)3]Li, underwent ring-closing dimerization upon heating to give, after subsequent hydrolysis, 4,8-dihydro-4,8-dihydroxy-p-diborino[2,3-b:5,6-b′]dithiophene - a cyclic diborinic acid. A computational study of the lithiation of boronated thiophenes and furans proved that boronation decreases ring-proton acidity. This effect is much stronger for the boronic "ate" complexes than for the corresponding neutral BDEA esters. Calculations of the transition states have shown that the specific directing effect of boronate groups in 3-thienyl derivatives is due to intramolecular oxygen-lithium coordination.