N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester
- Product Name
- N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester
- CAS No.
- 286961-14-6
- Chemical Name
- N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester
- Synonyms
- tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate;N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester;EOS-60794;3,6-DIHYDR;PyridineC5H5N;N-BOC-1.2.5.6;N-BOC-1.2.5.8-;tert-butyl 4-(4;1-Boc-1,2,5,6-tetrahydrop...;6-tetrahydropyridine-1-carboxylate
- CBNumber
- CB3290758
- Molecular Formula
- C16H28BNO4
- Formula Weight
- 309.21
- MOL File
- 286961-14-6.mol
N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester Property
- Melting point:
- 114.0 to 118.0 °C
- Boiling point:
- 348.0±52.0 °C(Predicted)
- Density
- 1.05±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Chloroform (Sparingly), Dichloromethane (Sparingly), DMSO (Slightly)
- pka
- -1.21±0.40(Predicted)
- form
- Solid
- color
- white to off-white
- Water Solubility
- Soluble in most organic solvents. Insoluble in water.
- InChI
- 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
- InChIKey
- VVDCRJGWILREQH-UHFFFAOYSA-N
- SMILES
- C1N(C(OC(C)(C)C)=O)CC=C(B2OC(C)(C)C(C)(C)O2)C1
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 706531
- Product name
- N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester
- Purity
- 95%
- Packaging
- 1g
- Price
- $142
- Updated
- 2025/07/31
- Product number
- B4051
- Product name
- 1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
- Purity
- >98.0%(GC)(T)
- Packaging
- 1g
- Price
- $92
- Updated
- 2025/07/31
- Product number
- D453413
- Product name
- 3,6-Dihydro-2H-pyridine-1-N-Boc-4-boronicacid,pinacolester
- Packaging
- 500mg
- Price
- $65
- Updated
- 2021/12/16
- Product number
- 263778
- Product name
- N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester
- Packaging
- 1g
- Price
- $333
- Updated
- 2021/12/16
- Product number
- D453413
- Product name
- 3,6-Dihydro-2H-pyridine-1-N-Boc-4-boronicacid,pinacolester
- Packaging
- 100mg
- Price
- $45
- Updated
- 2021/12/16
N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester Chemical Properties,Usage,Production
Chemical Properties
off-white powder
Uses
Reagent used for suzuki-Miyaura cross-coupling using palladium phosphine catalyst, palladium-catalyzed ligand-controlled regioselective Suzuki coupling, wrenchnolol derivative optimized for gene activation in cells. Also used in Preparation of several enzymatic inhibitors and receptor ligands, orally active anaplastic lymphoma kinase inhibitors and oxazolecarboxamides as diacylglycerol acyltransferase-1 inhibitors for treatment of obesity and diabetes.
Uses
N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester is an intermediate for organic synthesis and pharmaceutical research and development, and can be used for suzuki reaction.
Synthesis
138647-49-1
73183-34-3
375853-82-0
The general procedure for the synthesis of 1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine from tert-butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate and bipinacolato pinacol ester was carried out as follows: to a dry reaction flask, bis(pinacolato)diboron ( 3.37 g, 13.28 mmol), potassium acetate (KOAc, 3.58 g, 36.46 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (PDCL2DPPF, 0.27 g, 0.36 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (dppf, 0.2 g, 0.36 mmol) to a dry reaction flask, and the reaction system was subsequently flushed with argon to flush the reaction system. A solution of tert-butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate (4.00 g, 12.07 mmol) in dioxane (35 mL) was added, and the reaction mixture was stirred at 80 °C overnight. After completion of the reaction, it was cooled to room temperature, diluted with water (50 mL) and extracted with ethyl acetate (EtOAc, 50 mL). The organic layer was separated, washed with saturated saline (50 mL), dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the crude product was purified by fast column chromatography (eluent ratio of 9:1 hexane:ethyl acetate) to give the target product as a white solid (4.5 g, 100% yield).
References
[1] Patent: WO2004/58727, 2004, A1. Location in patent: Page 53-54
[2] Patent: WO2014/100501, 2014, A1. Location in patent: Paragraph 00727; 00728
[3] Patent: WO2015/200534, A2. Location in patent: Paragraph 00297; 00586; 00643
[3] Patent: , 2015, . Location in patent: Paragraph 00297; 00586; 00643
[5] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 59-60
N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester manufacturers
- Product
- N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester 286961-14-6
- Price
- US $1.00/kg
- Min. Order
- 0.10000000149011612kg
- Purity
- 99%
- Supply Ability
- 200KG
- Release date
- 2024-05-24
- Product
- N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester 286961-14-6
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2022-09-22
- Product
- N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester 286961-14-6
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%min
- Supply Ability
- 20 tons
- Release date
- 2025-03-03