Description

4-(Hydroxymethyl)benzeneboronic acid pinacol ester (CAS No. 302348-51-2) is a high-purity boronic ester compound with the molecular formula C₁₃H₁₉BO₃. This organoboron reagent features a hydroxymethyl functional group attached to a phenyl ring, which is further stabilized by the pinacol boronic ester moiety. Its IUPAC name is [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol. This compound is widely utilized in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry, due to its excellent stability and reactivity. It is supplied as a white to off-white crystalline powder with a typical purity of ≥95% (HPLC). Suitable for use in pharmaceutical research, materials science, and chemical synthesis, this reagent is packaged under inert gas to ensure maximum stability and shelf life. Store in a cool, dry place away from moisture and oxidizing agents.

Properties

• CAS Number: 302348-51-2
• Complexity: 254
• IUPAC Name: [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol
• InChI: InChI=1S/C13H19BO3/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-8,15H,9H2,1-4H3
• InChI Key: GZZBZWITJNATOD-UHFFFAOYSA-N
• Exact Mass: 234.1427246
• Molecular Formula: C13H19BO3
• Molecular Weight: 234.10
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)CO
• Topological: 38.7
• Monoisotopic Mass: 234.1427246
• Synonyms: 4-(HYDROXYMETHYL)BENZENEBORONIC ACID PINACOL ESTER, 805-003-8, 302348-51-2, (4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL)METHANOL, 4-(HYDROXYMETHYL)PHENYLBORONIC ACID PINACOL ESTER, 4-HYDROXYMETHYLPHENYLBORONIC ACID, PINACOL ESTER, [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol, Benzenemethanol, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, MFCD09837617, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZYL ALCOHOL, [4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol, 4-Hydroxymethylphenylboronic acid pinacol ester, SCHEMBL1285032, CHEMBL4443690, DTXSID70464771, BCP19655, 2-[4-(Hydroxymethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, AKOS015949561, AS-2366, CS-W005313, FH39763, SY107021, T3496, H10378, EN300-1614321, 4-(Hydroxymethyl)phenylboronic acid pinacol ester, 97%, Z3234952715, (4-(HYDROXYMETHYL)PHENYL)BORONIC ACID PINACOL ESTER, (4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol…, [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanol

Application

4-(Hydroxymethyl)benzeneboronic acid pinacol ester is a versatile building block in organic synthesis, particularly in the preparation of biaryl compounds via Suzuki-Miyaura coupling. It is employed in the synthesis of pharmaceutical intermediates, liquid crystals, and advanced materials. The hydroxymethyl group allows for further functionalization, making it valuable in polymer chemistry and drug discovery. Its stability under various conditions makes it a preferred choice for multi-step synthetic routes.

Safety and Hazards

GHS Hazard Statements

• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statements

• P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501

Hazard Classes and Categories

• Acute Tox. 4 (50%)
• Acute Tox. 4 (50%)
• Acute Tox. 4 (50%)

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