Description

1-Carbobenzoxy-1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (CAS: 286961-15-7) is a high-purity boronic ester derivative designed for advanced synthetic applications in medicinal chemistry and organic synthesis. With the molecular formula C₁₉H₂₆BNO₄, this compound features a carbobenzoxy (Cbz) protecting group and a pinacol boronate moiety, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed transformations. Its IUPAC name is benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate, and it is supplied as a stable, crystalline solid under inert conditions to ensure optimal reactivity. Ideal for researchers developing pharmaceuticals, agrochemicals, or functional materials, this reagent offers exceptional compatibility with sensitive functional groups.

Properties

• CAS Number: 286961-15-7
• Complexity: 510
• IUPAC Name: benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate
• InChI: InChI=1S/C19H26BNO4/c1-18(2)19(3,4)25-20(24-18)16-10-12-21(13-11-16)17(22)23-14-15-8-6-5-7-9-15/h5-10H,11-14H2,1-4H3
• InChI Key: QDSFHRPYZPQWEJ-UHFFFAOYSA-N
• Exact Mass: 343.1954885
• Molecular Formula: C19H26BNO4
• Molecular Weight: 343.2
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCN(CC2)C(=O)OCC3=CC=CC=C3
• Topological: 48
• Monoisotopic Mass: 343.1954885
• Synonyms: 1-Carbobenzoxy-1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 854-741-7, 286961-15-7, benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate, N-Cbz-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester, Benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate, N-Cbz-3,6-Dihydro-2H-pyridine-4-boronic acid pinacol ester, 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester, 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, phenylmethyl ester, benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate, MFCD11521562, N-Cbz-1,2,3,6-tetrahydropyridine-4-boronic acid, pinacol ester, 1-Benzyloxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester, 1-Cbz-1,2,3,6-tetrahydropyridine-4-boronic Acid Pinacol Ester, QDSFHRPYZPQWEJ-UHFFFAOYSA-N, benzyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate, SCHEMBL1103983, DTXSID00461435, Benzyl 4-(4,4,5,5-Tetrameth, BCP14209, CS-B0400, AKOS015904477, (1-((BENZYLOXY)CARBONYL)-1,2,3,6-TETRAHYDROPYRIDIN-4-YL)BORONIC ACID PINACOL ESTER, NCGC00663095-01, benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate, DS-13191, HY-32685, PD199915, SY026133, C3243, A22998, EN300-212704, Z1741977412, 2-[1-(Carbobenzoxy)-1,2,3,6-tetrahydro-4-pyridyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, phenylmethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate

Application

This compound is widely used as a key intermediate in the synthesis of bioactive molecules, particularly in the construction of heterocyclic scaffolds via Pd-catalyzed cross-coupling reactions. Its boronate ester group enables efficient Suzuki-Miyaura couplings with aryl halides, while the Cbz-protected amine allows for selective deprotection in multistep syntheses. Applications include the preparation of piperidine-based drug candidates, kinase inhibitors, and boron-containing probes for chemical biology.

Safety and Hazards

GHS Hazard Statements

• H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (66.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (66.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
• H413 (33.3%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P273, 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 (66.7%)
• Skin Irrit. 2 (66.7%)
• Eye Irrit. 2A (66.7%)
• STOT SE 3 (66.7%)
• Aquatic Chronic 4 (33.3%)

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