Description

4,4,5,5-Tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane (CAS: 256652-04-7) is a highly versatile boronic ester compound with the molecular formula C₁₆H₁₉BO₂. This organoboron reagent is widely used in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry, due to its stability and reactivity. The pinacol ester group enhances its shelf life and handling convenience, making it a preferred choice for researchers. It is particularly valuable in the synthesis of complex organic molecules, pharmaceuticals, and advanced materials. Available in high purity grades, this compound is rigorously tested to ensure consistency and performance in sensitive applications.

Properties

• CAS Number: 256652-04-7
• Complexity: 324
• IUPAC Name: 4,4,5,5-tetramethyl-2-(2-naphthyl)-1,3,2-dioxaborolane
• InChI: InChI=1S/C16H19BO2/c1-15(2)16(3,4)19-17(18-15)14-10-9-12-7-5-6-8-13(12)11-14/h5-11H,1-4H3
• InChI Key: SPPZBAGKKBHZRW-UHFFFAOYSA-N
• Exact Mass: 254.1478100
• Molecular Formula: C16H19BO2
• Molecular Weight: 254.1
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=CC=CC=C3C=C2
• Topological: 18.5
• Monoisotopic Mass: 254.1478100
• Synonyms: 256652-04-7, 4,4,5,5-Tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane, Naphthalene-2-boronic acid, pinacol ester, Naphthalene-2-boronic acid pinacol ester, 4,4,5,5-tetramethyl-2-(2-naphthyl)-1,3,2-dioxaborolane, 4,4,5,5-tetramethyl-2-naphthalen-2-yl-1,3,2-dioxaborolane, MFCD05663868, 4,4,5,5-Tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane;2-Naphthaleneboronic acid pinacol ester;2-Napthaleneboronic acid, pinacol ester, 1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-(2-NAPHTHALENYL)-, SCHEMBL120527, DTXSID50444450, SPPZBAGKKBHZRW-UHFFFAOYSA-N, 4,4,5,5-TETRAMETHYL-2-(2-NAPHTHALENYL)-1,3,2-DIOXABOROLANE, AKOS015960148, 2-Naphthaleneboronic acid,pinacol ester, AB21984, 2-Napthaleneboronic acid, pinacol ester, SY024022, CS-0041414, T3298, EN300-1425706, Naphthalene-2-boronic acid pinacol ester, AldrichCPR, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene

Application

This compound is extensively employed in palladium-catalyzed cross-coupling reactions to form biaryl structures, a key step in drug discovery and material science. It serves as a critical intermediate in the synthesis of pharmaceuticals, agrochemicals, and OLED materials. Its stability under various conditions makes it suitable for multi-step synthetic routes. Researchers also utilize it in protodeboronation studies and as a building block for functionalized naphthalene derivatives.

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