3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
- Product Name
- 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
- CAS No.
- 329214-79-1
- Chemical Name
- 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
- Synonyms
- 3-PYRIDYLBORONIC ACID PINACOL ESTER;3-PYRIDINEBORONIC ACID PINACOL ESTER;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin;AKOS BRN-1142;3-Pyridineboronic;Pyridine-3-boronic acid p...;3-Pyridineboronic Acid PinacoL;Pinacolesterpyridinyl-3-boronicacid;3-pyrdineboronic acid pinacol ester;3-Pyridinylboronic acid pinacol ester
- CBNumber
- CB8190239
- Molecular Formula
- C11H16BNO2
- Formula Weight
- 205.06
- MOL File
- 329214-79-1.mol
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Property
- Melting point:
- 102-104.4 °C(lit.)
- Boiling point:
- 300.9±15.0 °C(Predicted)
- Density
- 1.03±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- soluble in Acetone
- pka
- 5.22±0.12(Predicted)
- form
- Crystalline Powder
- color
- White
- Water Solubility
- Insoluble
- InChI
- InChI=1S/C11H16BNO2/c1-10(2)11(3,4)15-12(14-10)9-6-5-7-13-8-9/h5-8H,1-4H3
- InChIKey
- XEMDFESAXKSEGI-UHFFFAOYSA-N
- SMILES
- C1=NC=CC=C1B1OC(C)(C)C(C)(C)O1
- CAS DataBase Reference
- 329214-79-1(CAS DataBase Reference)
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.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 576565
- Product name
- 3-Pyridineboronic acid pinacol ester
- Purity
- 97%
- Packaging
- 1g
- Price
- $95.64
- Updated
- 2025/07/31
- Product number
- 576565
- Product name
- 3-Pyridineboronic acid pinacol ester
- Purity
- 97%
- Packaging
- 5g
- Price
- $226
- Updated
- 2025/07/31
- Product number
- T2345
- Product name
- 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
- Purity
- >98.0%(GC)(T)
- Packaging
- 1g
- Price
- $21
- Updated
- 2025/07/31
- Product number
- T2345
- Product name
- 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
- Purity
- >98.0%(GC)(T)
- Packaging
- 5g
- Price
- $82
- Updated
- 2025/07/31
- Product number
- T2345
- Product name
- 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
- Purity
- >98.0%(GC)(T)
- Packaging
- 25g
- Price
- $327
- Updated
- 2025/07/31
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical Properties,Usage,Production
Chemical Properties
white crystalline powder
Uses
3-Pyridineboronic Acid Pinacol Ester is an organoborane compound used in the preparation of polyazatriaryl ligands by sequential borylation/Suzuki-Miyaura coupling. 3-Pyridineboronic Acid Pinacol Ester is used in the preparation of pyrrolo[2,3-b]pyridine derivatives as kinase modulators.
Uses
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine is an organoborane compound used in the preparation of of polyazatriaryl ligands by sequential borylation/Suzuki-Miyaura coupling. 3-Pyridineboronic Acid Pinacol E ster is used in the preparation of pyrrolo[2,3-b]pyridine derivatives as kinase modulators.
Synthesis
626-60-8
73183-34-3
329214-79-1
In a nitrogen-protected glove box, a benzene solution of silica-3p-TPP ([P] content 0.11 mmol/g, 45.5 mg, 0.005 mmol P, 1 mol% P), anhydrous degassed benzene (0.8 mL), and [PdCl(η3-cinnamyl)]2 (0.65 mg, 0.00125 mmol, 0.5 mol% Pd) (0.2 mL) was added sequentially to an oven-dried 10 mL glass tube pre-fitted with a magnetic stirrer. After stirring for 5 min, KOAc (147 mg, 1.5 mmol), bis(pinacolato)diboron (2,140 mg, 0.55 mmol) and 3-chloropyridine (63.3 mg, 0.50 mmol) were added sequentially. The reaction tube was sealed with a screw cap and then removed from the glove box, and the reaction was stirred at 25°C for 10 hours. After completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad (eluting with Et2O) and the filtrate was concentrated under reduced pressure. To the residue was added the internal standard 1,1,2,2-tetrachloroethane, and the yield of the product 3-pyridineboronic acid pinacol ester was 95% as determined by 1H NMR. The crude product was purified by silica gel column chromatography to afford the target compound 3-pyridineboronic acid pinacol ester (87.0 mg, 0.40 mmol, 80% yield).
References
[1] ChemCatChem, 2014, vol. 6, # 5, p. 1340 - 1348
[2] RSC Advances, 2018, vol. 8, # 25, p. 13643 - 13648
[3] Angewandte Chemie - International Edition, 2007, vol. 46, # 28, p. 5359 - 5363
[4] Chemistry Letters, 2014, vol. 43, # 5, p. 584 - 586
[5] Patent: WO2010/110782, 2010, A1. Location in patent: Page/Page column 46-47
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Preparation Products And Raw materials
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View Lastest Price from 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine manufacturers
- Product
- 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 329214-79-1
- Price
- US $200.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%, 99.5% Sublimated
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2023-12-30
- Product
- 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 329214-79-1
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-11
- Product
- 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 329214-79-1
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-09