Description

2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (CAS No. 445264-61-9) is a high-purity boronic ester derivative with the molecular formula C₁₂H₁₈BNO₃. This compound features a pyridine core functionalized with a methoxy group at the 2-position and a pinacol boronate ester at the 5-position, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions. Its stable dioxaborolane ring ensures excellent shelf-life and handling properties under inert conditions. Ideal for pharmaceutical research, agrochemical development, and materials science, 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: 445264-61-9
• Complexity: 267
• IUPAC Name: 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• InChI: InChI=1S/C12H18BNO3/c1-11(2)12(3,4)17-13(16-11)9-6-7-10(15-5)14-8-9/h6-8H,1-5H3
• InChI Key: QOGNDJLSYMJGPP-UHFFFAOYSA-N
• Exact Mass: 235.1379736
• Molecular Formula: C12H18BNO3
• Molecular Weight: 235.09
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(C=C2)OC
• Topological: 40.6
• Monoisotopic Mass: 235.1379736
• Synonyms: 445264-61-9, 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, DTXSID40584511, DTXCID50535276, 625-864-1, 2-Methoxyl-5-pyridineboronic acid pinacol ester, 2-Methoxypyridine-5-boronic acid pinacol ester, 2-METHOXYPYRIDINE-5-BORONIC ACID, PINACOL ESTER, 6-Methoxypyridine-3-boronic acid pinacol ester, MFCD05663858, 2-Methoxy-5-pyridineboronic acid pinacol ester, QOGNDJLSYMJGPP-UHFFFAOYSA-N, 6-Methoxy-3-pyridylboronic Acid Pinacol Ester, Pyridine, 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 6-methoxypyridin-3-ylboronic acid pinacol ester, SCHEMBL837572, 2-methoxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, AKOS005259449, AB21962, CS-W008133, NCGC00662772-01, AC-24359, DS-13984, SY022302, DB-010466, M2650, EN300-316760, 2-Methoxypyridine-5-boronic acid pinacol ester, 97%, Z2044774133, (6-METHOXYPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER, 2-(6-Methoxy-3-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-pyridine, 2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine, 6-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Application

This boronic ester is widely used as a key building block in palladium-catalyzed cross-coupling reactions to construct biaryl systems in drug discovery. It serves as a precursor for functionalized pyridine derivatives in medicinal chemistry and materials science. The compound’s stability and reactivity make it particularly valuable for synthesizing complex molecules in controlled environments.

Safety and Hazards

GHS Hazard Statements

• H302 (28.1%): 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 (35.9%): 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 (28.1%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (35.9%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.