N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester, CAS No. 286961-14-6

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286961-14-6

Catalog No. EBD54435

CAS 286961-14-6

Name N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester

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Basic Information

Synonyms: Tert-butyl 5,6-dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-1(2H)-carboxylate N-Boc-1,2,5,6-tetrahydropyridine-4-(pinacolato)boronate tert-butyl4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate tert-butyl4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate 3,6-Dihydro-2H-pyridine-1-N-Boc-4-boronicacidpinacolester Tert-Butyl5,6-Dihydro-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine-1(2H)-Carboxylate 4-(4,4,5,5-Tetramethyl-[1,3,2]Dioxaborolan-2-Yl)-3,6-Dihydro-2H-Pyridine-1-CarboxylicAcidTert-ButylEster tert-butyl4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate 3,6-Dihydro-2H-pyridine-1-tert-butoxycarbonyl-4-boronicacidpinacolester N-Boc-1,2,5,6-tetrahydropyridine-4-boronicacidpinacolester

Molecular Formula: C16H28BNO4

Molecular Weight: 309.21

MDL Number: MFCD03840345

Categories: Synthetic Chemistry > Organic Building Blocks > Amines Synthetic Chemistry > Organic Building Blocks > Boronic Acids and Boronic Esters Synthetic Chemistry > Organic Building Blocks > C-C Double and Triple Bonds Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates

Product Description:

N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester is a heterocyclic organoboron compound featuring a Boc-protected tetrahydropyridine ring and a pinacol boronate ester at the 4-position. The Boc group provides stability and ease of deprotection under mild acidic conditions, while the boronic ester moiety enables versatile cross-coupling reactions, particularly Suzuki-Miyaura couplings. This compound is primarily utilized as a key building block in medicinal chemistry for the synthesis of diverse bioactive molecules, including central nervous system agents, kinase inhibitors, and GPCR modulators. Its tetrahydropyridine scaffold is a common pharmacophore in drug discovery, and the boronate handle allows for late-stage functionalization to introduce aryl or heteroaryl groups. Additionally, it serves as a valuable synthetic intermediate in organic chemistry for constructing complex nitrogen-containing heterocycles. The compound is typically stored under inert atmosphere at low temperatures to prevent hydrolysis of the boronic ester. Its high reactivity and selectivity make it indispensable in both academic research and pharmaceutical process development.

Physical Properties

Melting Point: 100-114 °C

Boiling Point: 348.007 °C at 760 mmHg

Flash Point: 164.269 °C

Density: 1.055 g/cm3