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Chemistry
Organometallic Reagents
Organoboron
2,6-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
Chemistry
Organometallic Reagents
Heterocyclic Building Blocks Organic Building Blocks
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Pyridines Esters

[ CAS No. 693774-10-6 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 693774-10-6
Chemical Structure| 693774-10-6
Structure of 693774-10-6 *Storage: {[proInfo.prStorage]}

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Quality Control of [ 693774-10-6 ]

Purity: {[proInfo.showProBatch.pb_purity]}

COA GC NMR CNMR HPLC/UPLC LC-MS

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SDS

Product Details of [ 693774-10-6 ]

CAS No. :693774-10-6MDL No. :MFCD13195066
Formula :C13H20BNO2Boiling Point :317.2±42.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :233.11Pubchem ID :21980034
Synonyms :

Computed Properties of [ 693774-10-6 ]

TPSA : 31.4 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.62 Rotatable Bond Count : 1

Safety of [ 693774-10-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 693774-10-6 ]

  • Upstream synthesis route of [ 693774-10-6 ]

[ 693774-10-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 61676-62-8 ]
  • [ 693774-10-6 ]
YieldReaction ConditionsOperation in experiment
98.4%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 0.75 h;
Stage #2: at -78℃; for 3.00 h; 		Example 2A
2,6-Dimethyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine
A solution of 3-bromo-2,6-dimethylpyridine (5.10 g, 27.4 mmol) in anhydrous ether (160 ml) cooled to -78° C. under a nitrogen atmosphere was treated dropwise with n-butyl lithium (4.1 ml, 10 M in hexane) and stirred at -78° C. for 45 minutes. 2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (10.2 g, 54.8 mmol) in 20 ml of ether was added dropwise at -78° C. and stirred at -78° C. for 3 hours.
The mixture was quenched with 10 ml of isopropanol, and allowed to warm to room temperature. 150 ml of saturated aqueous NaCl solution was added.
The aqueous phase was separated and extracted with dichloromethane (100 ml*6).
The combined organic phases were dried and concentrated to provide the title compound as light brown oil (6.29 g, 98.4percent).
1H NMR (300 MHz, CDCl3) δ ppm 7.92 (d, J=7.46 Hz, 1H) 6.96 (d, J=7.80 Hz, 1H) 2.73 (s, 3H) 2.53 (s, 3H) 1.34 (s, 12H). MS: (M+H)+=234.
Reference： [1] Patent: US2007/66588, 2007, A1. Location in patent: Page/Page column 29-30
  • 2
  • [ 3430-31-7 ]
  • [ 73183-34-3 ]
  • [ 693774-10-6 ]
YieldReaction ConditionsOperation in experiment
9% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium acetate In 1,4-dioxaneInert atmosphere; Reflux 3-bromo-2,6-dimethylpyridine(11 g, 59.1 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2dioxaborolane)(19.52 g, 77 mmol), Potassiumacetate (6.95 g, 70.9 mmol), Tris(dibenzylideneacetone)palladium(0) (1.082 g, 1.182 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.939 g, 4.73 mmol) were charged into a reaction flask with 200 mL of dioxane. The mixture was degasssed withnitrogen, then was heated at reflux overnight. The reaction mixture was cooled to room temperature, then was diluted with 300 mL of water.This mixture was extracted two times with 300 mL ethyl acetate. The organics were combined and then washed with brine. The organics werecombined, were dried over magnesium sulfate, then were filtered and concentrated under vacuum. This crude residue was passed through asilica gel column using 120percentmethanol/DCM as the eluant yielding 2,6dimethyl3(4,4,5,5tetramethyl1,3,2dioxaborolan2yl)pyridine (1.2g, 5.15 mmol, 9percent yield).
Reference： [1] Patent: KR2015/83017, 2015, A. Location in patent: Paragraph 0200; 0201

Tags: 693774-10-6 synthesis path| 693774-10-6 SDS| 693774-10-6 COA| 693774-10-6 purity| 693774-10-6 application| 693774-10-6 NMR| 693774-10-6 COA| 693774-10-6 structure

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