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CAS No. : | 83004-13-1 | MDL No. : | MFCD11869660 |
Formula : | C7H8BrN | Boiling Point : | 217.9±20.0°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 186.05 | Pubchem ID : | 12954800 |
Synonyms : |
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TPSA :Topological Polar Surface Area | 12.9 | H-Bond Acceptor Count : | 1 |
XLogP3 : | 2.7 | H-Bond Donor Count : | 0 |
SP3 : | 0.29 | Rotatable Bond Count : | 1 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.616667 h; Inert atmosphere; Cooling with acetone-dry ice Stage #2: at -78 - 20℃; for 2.5 h; Inert atmosphere; Cooling with acetone-dry ice |
Preparation 23 Synthesis of 2-bromo-6-ethyl-pyridine Add under nitrogen a solution of 2.5 M n-butyllithium in hexanes (186.74 mL, 0.467 mol) over 41 min to a solution of diisopropylamine (68.7 mL, 0.488 mol) in tetrahydrofuran (745 mL, 9.16 mol) at -78° C. (dry-ice/acetone bath). Stir for 15 min and add 2-bromo-6-methylpyridine (49.3 mL, 0.424 mol) dropwise over 22 min. Stir 15 min, add methyl iodide (52.87 mL, 0.848 mol) dropwise over 1 hour and then warm to room temperature over 1.5 hour. Add water (250 mL) while cooling with a dry-ice/acetone bath and separate the layers. Extract the aqueous phase twice with ethyl acetate (300 mL). Combine the organic phases, concentrate and purify by silica gel chromatography, gradient eluding from 100:0 to 80:20 using hexanes:ethyl acetate, to give the title compound as a yellow oil (59.74 g, 75percent). 1H NMR (CDCl3) δ 1.28 (t, 3H), 2.80 (q, 2H), 7.11 (d, 1H), 7.27 (d, 1H), 7.45 (t, 1H). |
46% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h; Stage #2: at 20℃; for 3 h; |
To a solution of 2-bromo-6-methylpyridine (CAS 5315-25-3) (2.0 g, 11.7 mmol, 1.0 eq) in THF (10 mL) was added LDA (12.3 mL, 12.3 mmol, 1.05 eq) at -78 °C. After stirring at -78 °C for 1 h, CH3I (1.8 g, 12.3 mmol, 1.05 eq) was added to the mixture. The mixture was stirred at rt for 3 h. The mixture was quenched with sat. NH4C1 (2 mL), diluted with water (50 mL) and extracted with EA (2 x 100 mL). The combined organic phase was washed with brine and dried over Na2S04. After concentration, the residue was purified by silica gel chromatography with PE/EA (20/1) as eluent to give 2-bromo-6-ethylpyridine. 1.0 g, as a yellow solid, Y: 46percent. ESI-MS (M+H)+: 185.9, 187.9. |
46% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h; Stage #2: at 20℃; for 3 h; |
To a solution of 2-bromo-6-methylpyridine (CAS 53 15-25-3) (2.0 g, 11.7 mmol, 1.0 eq) in THF (10 mL) was added LDA (12.3 mL, 12.3 mmol, 1.05 eq) at -78 °C. After stirring at -78°C for 1 h, CH3I (1.8 g, 12.3 mmol, 1.05 eq) was added to the mixture. The mixture was stirred atrt for 3 h. The mixture was quenched with sat. NH4C1 (2 mL), diluted with water (50 mL) and extracted with EA (2 x 100 mL). The combined organic phase was washed with brine and dried over Na2504. After concentration, the residue was purified by silica gel chromatography with PE/EA (20/1) as eluent to give 2-bromo-6-ethylpyridine. 1.0 g, as a yellow solid, Y: 46percent. ESIMS (M+H): 185.9, 187.9. |