Description

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (CAS No. 1214264-88-6) is a highly specialized organoboron compound with the molecular formula C₁₆H₂₀B₂N₂O₂. This unique bicyclic structure combines a pinacol boronate ester with a diazaborinine moiety, offering exceptional reactivity for cross-coupling reactions and other boron-mediated transformations. The compound is supplied as a stable solid with purity verified by ¹H NMR and HPLC analysis. Suitable for use under inert atmosphere, this reagent is particularly valuable for synthesizing complex heterocyclic systems in pharmaceutical research and materials science applications. Store in a cool, dry place away from moisture at 2-8°C.

Properties

• CAS Number: 1214264-88-6
• Complexity: 410
• IUPAC Name: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4-diaza-3-boratricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene
• InChI: InChI=1S/C16H20B2N2O2/c1-15(2)16(3,4)22-18(21-15)17-19-12-9-5-7-11-8-6-10-13(20-17)14(11)12/h5-10,19-20H,1-4H3
• InChI Key: WWUSOISWGYNXKX-UHFFFAOYSA-N
• Exact Mass: 294.1710882
• Molecular Formula: C16H20B2N2O2
• Molecular Weight: 294.0
• SMILES: B1(NC2=CC=CC3=C2C(=CC=C3)N1)B4OC(C(O4)(C)C)(C)C
• Topological: 42.5
• Monoisotopic Mass: 294.1710882
• Synonyms: 1214264-88-6, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, 1-pinacolato-2-(1,8)diamo-naphthalenylborane, MFCD27980593, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4-diaza-3-boratricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4-diaza-3-boratricyclo[7.3.1.0(1)(3)]trideca-1(13),5,7,9,11-pentaene, (pin)B-B(dan), SCHEMBL21503776, C16H20B2N2O2, ZB0282, 1H-Naphtho[1,8-de][1,3,2]diazaborinine-2(3H)-boronic Acid Pinacol Ester, AKOS025146553, AS-2877, SB73763, SY113214, DB-103589, CS-0153880, C71777, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4-diaza-3-boratricyclo[7.3.1.0^{5,13]trideca-1(12),5,7,9(13),10-pentaene, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4-diaza-3-boratricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4-diaza-3-boratricyclo[7.3.1.0trideca-1(13),5,7,9,11-pentaene, 3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4-diaza-3-boratricyclo-[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11- pentaene, 3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4-diaza-3-boratricyclo-[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene

Application

This compound serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions for constructing polycyclic aromatic systems. Its unique structure enables the synthesis of boron-doped polycyclic aromatic hydrocarbons (PAHs) with potential applications in organic electronics. Researchers utilize this reagent to create novel luminescent materials and pharmaceutical intermediates with enhanced biological activity. The diazaborinine moiety offers interesting coordination chemistry possibilities for catalyst design.

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