Description

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (CAS No. 269409-97-4) is a high-purity boronic ester derivative with the molecular formula C₁₂H₁₇BO₃. This compound features a phenol group ortho-substituted with a 4,4,5,5-tetramethyl-1,3,2-dioxaborolane moiety, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions and other boron-mediated transformations. Its stable dioxaborolane ring ensures excellent shelf-life and handling properties under inert conditions. Ideal for pharmaceutical, agrochemical, and materials science research, this reagent is supplied as a crystalline solid with ≥95% purity (HPLC). Store under nitrogen at 2-8°C to maintain stability.

Properties

• CAS Number: 269409-97-4
• Complexity: 249
• IUPAC Name: 2-(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)9-7-5-6-8-10(9)14/h5-8,14H,1-4H3
• InChI Key: VLROJECCXBBKPZ-UHFFFAOYSA-N
• Exact Mass: 220.1270746
• Molecular Formula: C12H17BO3
• Molecular Weight: 220.07
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2O
• Topological: 38.7
• Monoisotopic Mass: 220.1270746
• Synonyms: 269409-97-4, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, DTXSID50370402, DTXCID30321437, 671-854-5, 2-Hydroxyphenylboronic acid pinacol ester, MFCD02093754, 2-hydroxyphenylboronic acid, pinacol ester, 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, phenol, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 2-Hydroxybenzeneboronic acid pinacol ester, 2-(2-Hydroxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)phenol, MY22UL2B7N, (2-HYDROXYPHENYL)BORONIC ACID PINACOL ESTER, SCHEMBL333869, 2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol, UKA40997, AKOS015950769, AB10830, AS-3008, CS-W008935, NCGC00663021-01, SY025275, 2-Hydroxyphenyl boronic acid pinacol ester, DS-016435, T1952, 2-Hydroxyphenylboronic acid pinacol ester, 98%, EN300-303427, F14959, 4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl-phenol, Z1741960626, 2-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 2-(4,4,5,5,-tetramethyl-1.3.2-dioxaborolan-2-yl)phenol, 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenol, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2yl)-phenol, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenol, 2-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)phenol

Application

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol is widely used as a key building block in Suzuki-Miyaura cross-coupling reactions for synthesizing biaryl compounds in drug discovery. It serves as a protected boronic acid equivalent in peptide and polymer chemistry, enabling controlled functionalization. Researchers also employ it in the development of OLED materials and boron-containing catalysts due to its air-stable handling properties.

Safety and Hazards

GHS Hazard Statements

• H302 (89.1%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (97.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (89.1%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (97.8%)

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