2-(2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a bench‑stable crystalline boronate ester that couples efficiently under standard Suzuki‑Miyaura conditions despite the steric encumbrance of its ortho‑methyl groups. The pinacol ester of 2-(2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is far more stable than the free boronic acid, which tends to cyclotrimerize into the boroxine. Medicinal chemists employ 2-(2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to cap biaryl scaffolds, filling a shallow hydrophobic pocket and blocking metabolic oxidation. Cosperpharm guarantees that each lot of 2-(2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is free of the de‑borylated xylene by‑product, ensuring accurate stoichiometric control in coupling reactions.
|
Parameter |
Specification |
|
Product Name |
2-(2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
|
CAS Number |
325141-72-8 |
|
Molecular Formula |
C₁₄H₂₁BO₂ |
|
Molecular Weight |
232.13 g/mol |
|
Appearance |
White to off-white crystalline solid |
|
Melting Point |
46–47 °C (typical) |
|
Purity (GC/HPLC) |
≥98.0% |
|
Solubility |
Freely soluble in THF, dichloromethane, toluene; sparingly soluble in hexane, water |
|
Storage Condition |
2–8 °C, sealed under nitrogen, protect from moisture |
|
Shelf Life |
24 months under recommended conditions |
Q1: What is the typical Suzuki coupling protocol for this hindered boronate?
A: 1.2 equivalents of the boronate, 1.0 equivalent of aryl bromide, 3 mol% Pd(PPh₃)₄, 2 M Na₂CO₃ in DME/water, reflux for 12–18 h gives good yields.
Q2: Can this boronate be used in Buchwald‑Hartwig aminations?
A: No, it is a nucleophilic partner for Suzuki coupling. For amination, the corresponding bromide or iodide should be used.
Store 2-(2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane at 2–8 °C in a tightly sealed container under an atmosphere of dry argon or nitrogen. Protect from moisture and light. Under these conditions, the product retains ≥98% purity for at least 24 months.
Each batch undergoes:
● Gas chromatography (GC) – purity ≥97.0%
● Non‑aqueous titration – purity ≥97.0%
● Refractive index – confirmatory analysis
● ¹H NMR – structural verification
● Appearance – colorless to light yellow to light orange clear liquid
A comprehensive COA, MSDS (with full GHS information), and certificate of origin accompany every shipment.
|
Category |
Information |
|
GHS Classification |
Skin Irrit. 2 (H315), Eye Irrit. 2 (H319), STOT SE 3 (H335) |
|
Signal Word |
Warning |
|
Precautionary Statements |
P261, P280, P305+P351+P338 |
If your project calls for a sterically demanding arylboronate with proven performance, contact Cosperpharm’s organoboron team — we’ll provide a sample, a recommended coupling procedure, and a commercial quote in one consolidated response.
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No. 2 Yangguang 3rd Road, Duodao Chemical Cycle Industrial Park, Jingmen City, Hubei Province, China
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