Description

5-Hydroxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (CAS: 1029439-74-4) is a high-purity boronic ester derivative with the molecular formula C₁₃H₁₆BNO₃. This compound features a benzonitrile core functionalized with a hydroxyl group and a 4,4,5,5-tetramethyl-1,3,2-dioxaborolane moiety, making it a versatile intermediate in organic synthesis and pharmaceutical research. Its boronic ester group is particularly valuable for Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds under mild conditions. The product is supplied as a crystalline solid with ≥95% purity (HPLC), ensuring optimal performance in sensitive applications. Suitable for use in medicinal chemistry, materials science, and agrochemical development, this compound is packaged under inert conditions to maintain stability and shelf life.

Properties

• CAS Number: 1029439-74-4
• Complexity: 358
• IUPAC Name: 5-hydroxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
• InChI: InChI=1S/C13H16BNO3/c1-12(2)13(3,4)18-14(17-12)11-6-5-10(16)7-9(11)8-15/h5-7,16H,1-4H3
• InChI Key: GDRLDPGGUZWIPL-UHFFFAOYSA-N
• Exact Mass: 245.1223235
• Molecular Formula: C13H16BNO3
• Molecular Weight: 245.08
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=C(C=C2)O)C#N
• Topological: 62.5
• Monoisotopic Mass: 245.1223235
• Synonyms: 5-hydroxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, 1029439-74-4, 5-HYDROXY-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZONITRILE, 5-hydroxy-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, SCHEMBL257939, ERB43974, MB15479, AS-77973, DB-219514, CS-0089489, C14036, EN300-183336, 5-Hydroxybenzonitrile-2-boronic acid pinacol ester, Z1873915091

Application

5-Hydroxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is widely employed as a key building block in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryl compounds. Its boronic ester group facilitates efficient coupling with aryl halides, making it valuable in pharmaceutical and materials science research. The compound is also used in the development of fluorescent probes and sensors due to its reactive hydroxyl and nitrile functionalities. Researchers utilize it to create novel heterocyclic frameworks in medicinal chemistry. Additionally, it serves as a precursor in the synthesis of advanced organic electronic materials.

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