Description

2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (CAS No. 214360-62-0) is a high-purity boronic ester derivative with the molecular formula C₁₁H₁₅BBrNO₂. This compound is a valuable intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, where it serves as a versatile boron-containing building block for constructing complex heterocyclic frameworks. The presence of the bromine substituent at the 2-position of the pyridine ring enhances its reactivity in palladium-catalyzed transformations. The 4,4,5,5-tetramethyl-1,3,2-dioxaborolane protecting group ensures stability under various reaction conditions while allowing for efficient transmetalation in coupling reactions. This product is supplied as a crystalline solid with >95% purity (HPLC) and is rigorously tested for moisture sensitivity. Ideal for pharmaceutical research, materials science, and agrochemical development, it is packaged under inert gas to ensure maximum shelf life and reactivity.

Properties

• CAS Number: 214360-62-0
• Complexity: 257
• IUPAC Name: 2-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• InChI: InChI=1S/C11H15BBrNO2/c1-10(2)11(3,4)16-12(15-10)8-5-6-9(13)14-7-8/h5-7H,1-4H3
• InChI Key: MEGBELYYUPCOIQ-UHFFFAOYSA-N
• Exact Mass: 283.03792
• Molecular Formula: C11H15BBrNO2
• Molecular Weight: 283.96
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(C=C2)Br
• Topological: 31.4
• Monoisotopic Mass: 283.03792
• Synonyms: 214360-62-0, 2-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, DTXSID00383345, DTXCID70334369, 681-888-2, 2-Bromopyridine-5-boronic acid pinacol ester, 6-Bromopyridine-3-boronic acid pinacol ester, 2-Bromo-5-pyridylboronic acid pinacol ester, MFCD03412794, 2-Bromopyridine-5-boronic acid, pinacol ester, Pyridine, 2-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, SCHEMBL2099623, (6-BROMOPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER, 2-bromo-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, MEGBELYYUPCOIQ-UHFFFAOYSA-N, BCP14071, SBB052577, AKOS004116431, AB14440, CS-W010032, DS-1500, AC-33503, SY032176, 2-Bromo-5-pyridineboronic acid pinacol ester, A25318, EN300-187911, Z1741972826, 2-(6-bromo(3-pyridyl))-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-(6-bromopyridin-3-yl)-4,4,5,5-tetramethyl-1,3-dioxaborolane

Application

2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine is widely used as a key reagent in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryl compounds in medicinal chemistry. It serves as a crucial intermediate in the preparation of pharmaceutical candidates, particularly those containing pyridine scaffolds. The compound’s stability and reactivity make it suitable for constructing complex molecules in drug discovery programs. Researchers also utilize it in materials science for developing organic electronic materials and ligands for catalytic systems.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): 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 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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