706531

N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester

95%

• Synonym(s): (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
• Empirical Formula (Hill Notation): C₁₆H₂₈BNO₄
• CAS Number: 286961-14-6
• Molecular Weight: 309.21
• MDL number: MFCD03840345
• UNSPSC Code: 12352103
• PubChem Substance ID: 329762650
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 95%
• form: powder
• mp: 100-114 °C
• SMILES string: CC(C)(C)OC(=O)N1CCC(=CC1)B2OC(C)(C)C(C)(C)O2
• InChI: 1S/C16H28BNO4/c1-14(2,3)20-13(19)18-10-8-12(9-11-18)17-21-15(4,5)16(6,7)22-17/h8H,9-11H2,1-7H3
• InChI key: VVDCRJGWILREQH-UHFFFAOYSA-N

Description

General description

Boc-THP-Bpin is frequently used in metal catalyzed cross-coupling reactions, such as Suzuki-Miyaura and Negishi couplings.

Application

Reagent used for

• Suzuki-Miyaura cross-coupling using palladium phosphine catalyst
• Palladium-catalyzed ligand-controlled regioselective Suzuki coupling
• Palladium-catalyzed Suzuki-Miyaura coupling
• Suzuki coupling followed by iodolactonization reaction
• Wrenchnolol derivative optimized for gene activation in cells

Reagent used in Preparation of several enzymatic inhibitors and receptor ligands

• Orally active anaplastic lymphoma kinase inhibitors
• Oxazolecarboxamides as diacylglycerol acyltransferase-1 inhibitors for treatment of obesity and diabetes
• 4-arylpiperidinyl amides and N-arylpiperidin-3-yl-cyclopropanecarboxamides as novel melatonin receptor ligands
• Quinazoline analogs as glucocerebrosidase inhibitors with chaperone activity for treatment of Gaucher disease, a lysosomal storage disorder
• Arylpiperazine and piperidine ethers as dual acting norepinephrine reuptake inhibitors and 5-HT1A partial agonists

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves