N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester
N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (CAS 286961-14-6) is a valuable organoboron compound with the molecular formula C16H28BNO4 and a molecular weight of 309.21 g/mol. This compound serves as a key building block in organic synthesis, particularly in palladium-catalyzed cross-coupling reactions such as the Suzuki-Miyaura coupling. Its structure facilitates the introduction of substituted tetrahydropyridine moieties into complex molecules.
- IUPAC
- (1-tert-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)boronic acid pinacol ester,(N-tert-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)boronic acid pinacol ester,(N-tert-Butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)boronic acid pinacol ester,(N-tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester
- Synonyms
- 6-tetrahydropyridine-4-boronic acid pinacol ester286961-14-6C16H28BNO4(1-tert-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)boronic acid pinacol ester(N-tert-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)boronic acid pinacol ester(N-tert-Butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)boronic acid pinacol ester(N-tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester
Suzuki-Miyaura Cross-Coupling Reactions
This reagent is widely employed in Suzuki-Miyaura cross-coupling reactions, typically utilising palladium phosphine catalysts. It enables the formation of carbon-carbon bonds by reacting with organohalides or pseudohalides.
Ligand-Controlled Regioselective Coupling
It facilitates palladium-catalyzed, ligand-controlled regioselective Suzuki coupling reactions. This allows for precise control over the position of bond formation in synthetic pathways.
Preparation of Biologically Active Compounds
The compound is instrumental in the preparation of various enzyme inhibitors and receptor ligands. These include orally active anaplastic lymphoma kinase inhibitors and diacylglycerol acyltransferase-1 inhibitors for potential therapeutic applications.
Synthesis of Melatonin Receptor Ligands
It is used in the synthesis of novel melatonin receptor ligands, such as 4-arylpiperidinyl amides and N-arylpiperidin-3-yl-cyclopropanecarboxamides, relevant in medicinal chemistry research.
| Molecular weight | 309.21 |
|---|---|
| Empirical formula | C16H28BNO4 |
| Assay | 95% |
| Application | Reagent used for • Suzuki-Miyaura cross-coupling using palladium phosphine catalyst1 • Palladium-catalyzed ligand-controlled regioselective Suzuki coupling2 • Palladium-catalyzed Suzuki-Miyaura coupling3 • Suzuki coupling followed by iodolactonization reaction4 • Wrenchnolol derivative optimized for gene activation in cells5 Reagent used in Preparation of several enzymatic inhibitors and receptor ligands• Orally active anaplastic lymphoma kinase inhibitors6 • Oxazolecarboxamides as diacylglycerol acyltransferase-1 inhibitors for treatment of obesity and diabetes7 • 4-arylpiperidinyl amides and N-arylpiperidin-3-yl-cyclopropanecarboxamides as novel melatonin receptor ligands8 • Quinazoline analogs as glucocerebrosidase inhibitors with chaperone activity for treatm |
| Melting point | 100-114 °C |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 3 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester used for?
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N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester is primarily used as a reagent in Suzuki-Miyaura cross-coupling reactions and in the preparation of various enzyme inhibitors and receptor ligands for medicinal chemistry research.
What are the CAS number and molecular formula for this compound?
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The CAS number is 286961-14-6, and the empirical formula (Hill notation) is C16H28BNO4.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this product at a purity of 95%. It is supplied as a research-grade chemical, and TSS does not represent it as USP, BP, or EP grade.
How should N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester be handled safely?
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When handling, wear appropriate personal protective equipment, including eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter is recommended. Observe appropriate safety protocols for chemical handling.
Is this compound a controlled substance?
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The provided data does not indicate that this compound is a controlled substance.
How is this chemical exported and shipped?
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Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals. We ensure appropriate packaging and documentation for international shipments.
How can I request a quote or sample?
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Please contact our sales team via the website or email to request a quotation or a sample of N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester.
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