Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol (CAS: 1054483-78-1) is a high-purity boronic ester derivative with the molecular formula C₁₁H₁₆BNO₃. This compound features a pinacol-protected boronic acid group attached to a pyridin-2-ol scaffold, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed processes. Its stability under ambient conditions and compatibility with diverse reaction conditions make it ideal for pharmaceutical, agrochemical, and materials science research. The product is supplied as a white to off-white crystalline solid with ≥95% purity (HPLC), ensuring reliable performance in synthetic applications. Proper storage under inert atmosphere at 2-8°C is recommended to maintain stability.

Properties

• CAS Number: 1054483-78-1
• Complexity: 369
• IUPAC Name: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyridin-2-one
• InChI: InChI=1S/C11H16BNO3/c1-10(2)11(3,4)16-12(15-10)8-5-6-9(14)13-7-8/h5-7H,1-4H3,(H,13,14)
• InChI Key: WAUWXCUPDOXYKS-UHFFFAOYSA-N
• Exact Mass: 221.1223235
• Molecular Formula: C11H16BNO3
• Molecular Weight: 221.06
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CNC(=O)C=C2
• Topological: 47.6
• Monoisotopic Mass: 221.1223235
• Synonyms: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol, 690-572-3, 1054483-78-1, 6-HYDROXYPYRIDINE-3-BORONIC ACID PINACOL ESTER, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyridin-2-one, 6-Hydroxypyridine-3-boronic acid, pinacol ester, 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol, MFCD06795671, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one, WAUWXCUPDOXYKS-UHFFFAOYSA-N, 2-HYDROXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE, 2-Hydroxypyridine-5-boronic acid, pinacol ester, SCHEMBL506215, SCHEMBL2493257, CHEMBL4972157, (6-HYDROXYPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER, DTXSID70590387, SBB096080, AKOS005256881, AKOS032949745, AB29220, AS-2371, CS-W014746, SY026650, F10517, 6-hydroxy-pyridin-3-yl-boronic acid pinacol ester, 6-Hydroxypyridine-3-boronic acid pinacol ester, 97%, 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ol, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridin-2(1H)-one

Application

This compound serves as a key building block in the synthesis of biaryl structures via Suzuki-Miyaura coupling, particularly for introducing pyridin-2-ol moieties into complex molecules. It finds application in the development of pharmaceutical candidates, especially kinase inhibitors and receptor modulators. Researchers also utilize it in material science for creating boron-doped organic electronic materials. The pinacol ester group enhances stability while remaining reactive under standard cross-coupling conditions.

Safety and Hazards

GHS Hazard Statements

• H315 (97.6%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (97.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statements

• P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364

Hazard Classes and Categories

• Skin Irrit. 2 (97.6%)
• Eye Irrit. 2A (97.6%)

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