Description

Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate (CAS: 885693-20-9) is a high-purity boronic ester derivative widely used in Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed transformations. With the molecular formula C₁₆H₂₈BNO₄, this compound features a protected tetrahydropyridine scaffold with a pinacol boronate ester moiety, offering excellent stability and reactivity for synthetic applications. Its IUPAC name is tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate. This reagent is ideal for constructing complex heterocycles and pharmaceutical intermediates, provided in rigorously controlled conditions to ensure consistency for research and industrial use. Store under inert atmosphere at recommended temperatures to maintain integrity.

Properties

• CAS Number: 885693-20-9
• Complexity: 463
• IUPAC Name: tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate
• InChI: InChI=1S/C16H28BNO4/c1-14(2,3)20-13(19)18-10-8-9-12(11-18)17-21-15(4,5)16(6,7)22-17/h9H,8,10-11H2,1-7H3
• InChI Key: KEEIJBAOTMNSEN-UHFFFAOYSA-N
• Exact Mass: 309.2111385
• Molecular Formula: C16H28BNO4
• Molecular Weight: 309.2
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCCN(C2)C(=O)OC(C)(C)C
• Topological: 48
• Monoisotopic Mass: 309.2111385
• Synonyms: tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate, 828-445-3, 885693-20-9, tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate, 1-BOC-5,6-DIHYDRO-2H-PYRIDINE-3-BORONIC ACID PINACOL ESTER, TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE, tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate, MFCD10697911, 1-BOC-3,6-DIHYDRO-2H-PYRIDINE-5-BORONIC ACID PINACOL ESTER, N-Boc-1,2,5,6-tetrahydropyridine-3-boronic Acid Pinacol Ester, 1-(tert-Butoxycarbonyl)-1,2,5,6-tetrahydro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborol, tert-butyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate, KEEIJBAOTMNSEN-UHFFFAOYSA-N, SCHEMBL520363, DTXSID70678619, BBL102712, STL556518, AKOS015841253, CS-W005209, PB25300, (1-(TERT-BUTOXYCARBONYL)-1,2,5,6-TETRAHYDROPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER, NCGC00662679-01, 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylicacid tert-butyl ester, DS-13198, FT138899, SY008465, B5844, EN300-170563, Z1508686554, 1-(Boc)-1,2,5,6-tetrahydropyridine-3-boronic acid pinacol ester, 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester, 5-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester, tert-butyl 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE, tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate, 95%, tert-Butyl3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Application

This compound is a versatile building block in medicinal chemistry, particularly for the synthesis of bioactive molecules via Suzuki coupling. It enables efficient C-C bond formation in the preparation of piperidine-based scaffolds, common in CNS-targeting drugs. Researchers also employ it in fragment-based drug discovery and PROTAC development due to its boronate ester functionality.

Safety and Hazards

GHS Hazard Statements

• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (16.7%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (83.3%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (66.7%): 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, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (50%)
• Acute Tox. 4 (16.7%)
• Skin Irrit. 2 (83.3%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (50%)
• STOT SE 3 (66.7%)

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