Description

4,4,5,5-Tetramethyl-2-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-1,3,2-dioxaborolane (CAS: 850568-69-3) is a highly specialized boronic ester compound with the molecular formula C₁₇H₂₅BO₄. This organoboron reagent is widely utilized in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry. The compound features a pinacol boronate ester moiety coupled with a tetrahydro-2H-pyran-2-yl (THP) protected phenol, offering both stability and reactivity for selective transformations. With a purity grade suitable for research and industrial applications, this product is rigorously tested via HPLC, NMR, and mass spectrometry to ensure consistency and performance. Ideal for pharmaceutical intermediates, agrochemical synthesis, and material science research, it is supplied in moisture-resistant packaging to maintain integrity.

Properties

• CAS Number: 850568-69-3
• Complexity: 369
• IUPAC Name: 4,4,5,5-tetramethyl-2-(3-tetrahydropyran-2-yloxyphenyl)-1,3,2-dioxaborolane
• InChI: InChI=1S/C17H25BO4/c1-16(2)17(3,4)22-18(21-16)13-8-7-9-14(12-13)20-15-10-5-6-11-19-15/h7-9,12,15H,5-6,10-11H2,1-4H3
• InChI Key: RIOLVUFARFCCCE-UHFFFAOYSA-N
• Exact Mass: 304.1845894
• Molecular Formula: C17H25BO4
• Molecular Weight: 304.2
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC=C2)OC3CCCCO3
• Topological: 36.9
• Monoisotopic Mass: 304.1845894
• Synonyms: 850568-69-3, 3-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid pinacol ester, 4,4,5,5-tetramethyl-2-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-1,3,2-dioxaborolane, 4,4,5,5-tetramethyl-2-[3-(oxan-2-yloxy)phenyl]-1,3,2-dioxaborolane, 3-(TETRAHYDROPYRAN-2-YLOXY)PHENYLBORONIC ACID, PINACOL ESTER, MFCD06659834, SCHEMBL1118822, DTXSID80619073, RIOLVUFARFCCCE-UHFFFAOYSA-N, AKOS015968943, AB26435, CS-W012103, BS-23187, D71302, 2-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]oxane, 3-(2-Tetrahydro-2H-pyran-2-yloxy)benzeneboronic acid, pinacol ester, 3-(2-TETRAHYDRO-2H-PYRANOXY)PHENYLBORONIC ACID PINACOL ESTER, 3-(2-TETRAHYDROPYRANYLOXY)BENZENEBORONIC ACID PINACOL ESTER, 2-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}tetrahydro-2H-pyran

Application

This boronic ester is a key intermediate in Suzuki-Miyaura cross-coupling reactions, enabling the formation of biaryl structures essential in drug discovery. The THP-protected phenol enhances solubility and stability in organic solvents, making it suitable for multistep syntheses. Researchers value its compatibility with palladium catalysts for constructing complex molecular architectures in medicinal chemistry and materials science.

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