Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid (CAS No. 1010836-19-7) is a high-purity boronic ester derivative with the molecular formula C₁₁H₁₅BO₄S. This compound features a thiophene ring substituted with a carboxylic acid group at the 2-position and a pinacol boronate ester at the 4-position, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed transformations. Its robust structure ensures stability under various synthetic conditions, while the boronate ester moiety enhances reactivity in aryl-aryl bond formation. Ideal for pharmaceutical, agrochemical, and materials science research, this reagent is supplied as a crystalline solid with ≥95% purity (HPLC). Store under inert conditions at 2-8°C to maintain optimal stability.

Properties

• CAS Number: 1010836-19-7
• Complexity: 315
• IUPAC Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid
• InChI: InChI=1S/C11H15BO4S/c1-10(2)11(3,4)16-12(15-10)7-5-8(9(13)14)17-6-7/h5-6H,1-4H3,(H,13,14)
• InChI Key: ZDNZEHFXGXIPLX-UHFFFAOYSA-N
• Exact Mass: 254.0784103
• Molecular Formula: C11H15BO4S
• Molecular Weight: 254.11
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CSC(=C2)C(=O)O
• Topological: 84
• Monoisotopic Mass: 254.0784103
• Synonyms: 1010836-19-7, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid, 2-CARBOXYTHIOPHENE-4-BORONIC ACID PINACOL ESTER, 2-carboxythiophene-4-boronic acid, pinacol ester, 2-Thiophenecarboxylic acid, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 5-Carboxythiophene-3-boronic acid pinacol ester, MFCD08064045, SCHEMBL1130443, DTXSID60585984, AKOS015950007, AB43519, AT16138, PS-13016, CS-0168553, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylicacid, 2-Carboxythien-4-yl)boronic Acid Pinacol Ester; 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic Acid;

Application

This compound is widely used as a key building block in the synthesis of thiophene-based conjugated polymers for organic electronics, including OLEDs and photovoltaic devices. It serves as a precursor for Suzuki coupling reactions to create biaryl structures in medicinal chemistry. Researchers also employ it in the development of boron-containing probes for bioimaging and sensor applications.

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