Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (CAS No. 269409-70-3) is a high-purity boronic acid pinacol ester derivative widely utilized in organic synthesis, pharmaceuticals, and materials science. This compound features a phenol group tethered to a stable pinacol boronate ester, making it an excellent intermediate for Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern C-C bond formation. With the molecular formula C₁₂H₁₇BO₃, it offers exceptional reactivity while maintaining stability under standard conditions. Its crystalline form and ≥97% purity (by HPLC) ensure reproducibility in research and industrial applications. Ideal for functionalizing aromatic systems, this reagent is packaged under inert gas to prevent degradation and is compatible with anhydrous protocols. Suitable for use in drug discovery, polymer chemistry, and agrochemical development.

Properties

• CAS Number: 269409-70-3
• Complexity: 241
• IUPAC Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• InChI: InChI=1S/C12H17BO3/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8,14H,1-4H3
• InChI Key: BICZJRAGTCRORZ-UHFFFAOYSA-N
• Exact Mass: 220.1270746
• Molecular Formula: C12H17BO3
• Molecular Weight: 220.07
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)O
• Topological: 38.7
• Monoisotopic Mass: 220.1270746
• Synonyms: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 627-688-0, 269409-70-3, 4-Hydroxyphenylboronic acid pinacol ester, 4-hydroxyphenylboronic acid, pinacol ester, MFCD02093756, 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 2-(4-Hydroxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, PHENOL, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, (4-HYDROXYPHENYL)BORONIC ACID PINACOL ESTER, 4-Hydroxyphenylboronic acid pinacol cyclic ester, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol, SCHEMBL102562, S6BC78LC96, SCHEMBL16012911, 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenol, DTXSID70370404, 3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 4-hydroxyphenylboronate, AKOS015915429, AB10835, AS-2606, CS-W002879, FH33842, HY-W002879, PB42436, NCGC00662624-01, SY020873, 4-hydroxybenzene boronic acid pinacol ester, 4-hydroxybenzeneboronic acid, pinacol ester, T1954, 4-Hydroxyphenylboronic acid pinacol ester, 97%, EN300-316486, Z1741960628, 4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 4-(4,4,5,5-tetramethyl 1,3,2-dioxaborolan-2-yl-)phenol, 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)phenol, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2yl)phenol, 4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)phenol, 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenol, 4-[4,4,5,5tetramethyl-1,3,2-dioxaborolan-2-yl]-phenol, 4-(4,4,5,5-tetramethyl 1,3,2-dioxaborolan-2-yl-) phenol, 4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenol, 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol

This compound is primarily employed as a key building block in Suzuki-Miyaura cross-coupling reactions to synthesize biaryl structures prevalent in pharmaceuticals and OLED materials. It serves as a protected boronic acid precursor for controlled functionalization of phenol-containing scaffolds in medicinal chemistry. Researchers also leverage its stability to develop boron-based sensors and covalent organic frameworks (COFs).

Safety and Hazards

GHS Hazard Statements

• H315 (94.3%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (94.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (92.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (94.3%)
• Eye Irrit. 2 (94.3%)
• STOT SE 3 (92.5%)

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