tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate
- Product Name
- tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate
- CAS No.
- 1354356-24-3
- Chemical Name
- tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate
- Synonyms
- 6-Boc-3-pyridineboronic Acid Pinacol Ester;tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate;tert-butyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate;tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate;2-Pyridinecarboxylic acid, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-dimethylethyl ester
- CBNumber
- CB73161907
- Molecular Formula
- C16H24BNO4
- Formula Weight
- 305.18
- MOL File
- 1354356-24-3.mol
tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate Property
- Boiling point:
- 413.0±30.0 °C(Predicted)
- Density
- 1.07±0.1 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- pka
- 1.83±0.12(Predicted)
- Appearance
- White to light brown Solid
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
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
- B812708
- Product name
- Tert-Butyl5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Picolinate
- Packaging
- 100mg
- Price
- $90
- Updated
- 2021/12/16
- Product number
- B812708
- Product name
- Tert-Butyl5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Picolinate
- Packaging
- 500mg
- Price
- $350
- Updated
- 2021/12/16
- Product number
- 3330DT
- Product name
- Tert-Butyl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate
- Packaging
- 1g
- Price
- $420
- Updated
- 2021/12/16
- Product number
- CD11282129
- Product name
- tert-Butyl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate
- Purity
- 95+%
- Packaging
- 1g
- Price
- $486
- Updated
- 2021/12/16
- Product number
- 1354356243
- Product name
- tert-Butyl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate
- Packaging
- 1g
- Price
- $524.7
- Updated
- 2021/12/16
tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate Chemical Properties,Usage,Production
Synthesis
845306-08-3
73183-34-3
1354356-24-3
Step 1: Synthesis of tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate A 1,4-dioxane solution (3.69 mL) of tert-butyl 5-bromopyridine-2-carboxylate (0.50 g, 1.937 mmol), potassium acetate (0.380 g, 3.87 mmol), pinacol ester of bis(boronic acid) (0.590 g, 2.325 mmol), and DMSO (0.184 mL) were added to a reaction flask under argon gas protection. The mixture was deoxygenated by argon bubbling for 5 min followed by addition of PdCl2(dppf)-CH2Cl2 adduct (0.079 g, 0.097 mmol). Subsequently, the reaction mixture was stirred at 90°C for 3 hours. After completion of the reaction, it was cooled to room temperature and the reaction solution was extracted and layered with ethyl acetate (300 mL) and water (80 mL). The organic phase was washed with water (100 mL×2) and saturated saline in turn, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the crude product. The crude product was purified by ISCO silica gel column chromatography (n-hexane/ethyl acetate gradient elution, 24 g silica gel column), and the target fraction was collected and concentrated to afford 0.60 g (near quantitative yield) of tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate as a nearly white solid. The product was analyzed by HPLC (Method B) with a retention time of 2.07 min.1H NMR (400 MHz, chloroform-d) δ 9.05 (s, 1H), 8.17 (dd, J = 7.8, 1.7 Hz, 1H), 7.99 (dd, J = 7.7, 0.9 Hz, 1H), 1.28 (s, 9H), 1.25 (s, 12H).
References
[1] Patent: WO2012/125893, 2012, A1. Location in patent: Page/Page column 225-226
[2] Patent: WO2012/3189, 2012, A1. Location in patent: Page/Page column 112
tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate Preparation Products And Raw materials
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