![4,4,5,5-Tetramethyl-2-(2-methyl-[1,1'-biphenyl]-3-yl)-1,3,2-dioxaborolane](/upload/8820/4-4-5-5-tetramethyl-2-2-methyl-1-1-biphenyl-3-yl-1-3-2-dioxaborolane-24837.webp "4,4,5,5-Tetramethyl-2-(2-methyl-[1,1'-biphenyl]-3-yl)-1,3,2-dioxaborolane")
4,4,5,5-Tetramethyl-2-(2-methyl-[1,1'-biphenyl]-3-yl)-1,3,2-dioxaborolane is a key intermediate for the assembly of highly substituted terphenyls and biaryl ethers, where the boronate ester couples smoothly with aryl bromides, iodides, or triflates. The pinacol ester of 4,4,5,5-Tetramethyl-2-(2-methyl-[1,1'-biphenyl]-3-yl)-1,3,2-dioxaborolane is far more resistant to protodeboronation than the corresponding boronic acid, allowing reactions in aqueous‑basic media at elevated temperatures. Chemists use 4,4,5,5-Tetramethyl-2-(2-methyl-[1,1'-biphenyl]-3-yl)-1,3,2-dioxaborolane to rapidly elaborate the biphenyl core into potential kinase inhibitors or liquid crystal precursors. Cosperpharm verifies the identity of each batch of 4,4,5,5-Tetramethyl-2-(2-methyl-[1,1'-biphenyl]-3-yl)-1,3,2-dioxaborolane by ¹H NMR and ensures a purity that delivers consistent coupling yields.
|
Parameter |
Specification |
|
Product Name |
4,4,5,5-Tetramethyl-2-(2-methyl-[1,1'-biphenyl]-3-yl)-1,3,2-dioxaborolane |
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CAS Number |
2095412-05-6 |
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Molecular Formula |
C₁₉H₂₃BO₂ |
|
Molecular Weight |
294.20 g/mol |
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Appearance |
White to off-white crystalline powder or low-melting solid |
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Purity (HPLC/GC) |
≥98.0% |
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Solubility |
Soluble in THF, dichloromethane, toluene; sparingly soluble in hexane, water |
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Storage Condition |
2–8 °C, sealed under inert gas, protect from moisture |
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Shelf Life |
24 months under recommended conditions |
4,4,5,5-Tetramethyl-2-(2-methyl-[1,1'-biphenyl]-3-yl)-1,3,2-dioxaborolane is prepared by the palladium‑catalyzed borylation of 3‑bromo‑2‑methyl‑1,1'‑biphenyl with bis(pinacolato)diboron in the presence of potassium acetate and Pd(dppf)Cl₂ in anhydrous dioxane. After aqueous workup, the crude ester is purified by column chromatography or recrystallization from pentane.
Q1: What are the recommended Suzuki coupling conditions for this boronate?
A: 1.1 equiv of the boronate, 1.0 equiv of aryl bromide, 2 mol% Pd(PPh₃)₄, 2 M Na₂CO₃ in DME/water, 85 °C, 12–18 h.
Q2: Is this boronate stable under basic conditions?
A: The pinacol ester is moderately stable. For slow couplings, adding an additional 0.2 equiv after 12 h can compensate for minor protodeboronation.
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Category |
Information |
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GHS Classification |
Skin Irrit. 2 (H315), Eye Irrit. 2 (H319), STOT SE 3 (H335) |
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Signal Word |
Warning |
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Precautionary Statements |
P261, P280, P305+P351+P338 |
To explore how this biphenyl boronate can streamline your next terphenyl coupling, reach out to Cosperpharm’s organoboron specialist — we can provide a 1‑g evaluation sample and a technical note on ligand selection within your required timeframe.
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No. 2 Yangguang 3rd Road, Duodao Chemical Cycle Industrial Park, Jingmen City, Hubei Province, China
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