Description

4,4-Dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydronaphthalen-1(2H)-one (CAS: 1312464-78-0) is a high-purity boronate ester compound with the molecular formula C₁₈H₂₅BO₃. This organoboron reagent is widely utilized in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of complex organic frameworks in pharmaceutical and materials science research. The compound features a stable dioxaborolane ring, ensuring optimal reactivity and shelf-life under controlled conditions. Its rigid dihydronaphthalenone backbone enhances selectivity in coupling reactions, making it a valuable intermediate for constructing polycyclic aromatic systems. Supplied as a crystalline solid with ≥95% purity (HPLC), it is rigorously tested for moisture sensitivity and stored under inert gas to maintain integrity. Ideal for researchers seeking reliable boron-based building blocks for C-C bond formation.

Properties

• CAS Number: 1312464-78-0
• Complexity: 453
• IUPAC Name: 4,4-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tetralin-1-one
• InChI: InChI=1S/C18H25BO3/c1-16(2)10-9-15(20)13-11-12(7-8-14(13)16)19-21-17(3,4)18(5,6)22-19/h7-8,11H,9-10H2,1-6H3
• InChI Key: PGGVVYKLXWRCGK-UHFFFAOYSA-N
• Exact Mass: 300.1896748
• Molecular Formula: C18H25BO3
• Molecular Weight: 300.2
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)C(CCC3=O)(C)C
• Topological: 35.5
• Monoisotopic Mass: 300.1896748
• Synonyms: 4,4-Dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydronaphthalen-1(2H)-one, 1312464-78-0, SCHEMBL2223742, PGGVVYKLXWRCGK-UHFFFAOYSA-N, DB-193537, CS-0369255, 3,4-Dihydro-4,4-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1(2h)-naphthalenone, 4,4-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-naphthalen-1-one

Application

This boronate ester is primarily employed in palladium-catalyzed cross-coupling reactions to synthesize biaryl structures prevalent in drug discovery. It serves as a key precursor for pharmaceutical intermediates, particularly in developing kinase inhibitors and anticancer agents. The compound’s stability in air-sensitive environments makes it suitable for high-throughput screening of novel organic electronic materials.

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