5-Bromo-2-(dimethylamino)pyridine Chemical Properties

Melting point:

69-71 °C

Boiling point:

253.5±20.0 °C(Predicted)

Density 

1.469±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

5.31±0.10(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C7H9BrN2/c1-10(2)7-4-3-6(8)5-9-7/h3-5H,1-2H3

InChIKey

XIMCGXXYEMOWQP-UHFFFAOYSA-N

SMILES

C1(N(C)C)=NC=C(Br)C=C1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Hazard Note 

Irritant

HS Code 

2933399990

5-Bromo-2-(dimethylamino)pyridine Usage And Synthesis

Synthesis

Step 64a: Synthesis of 5-bromo-N,N-dimethylpyridin-2-amine (Compound 0601-114) To a solution of 5-bromopyridin-2-amine (1.0 g, 5.8 mmol) in tetrahydrofuran (THF, 25 mL) was added sodium hydride (NaH, 60% dispersed in mineral oil, 0.92 g, 23.1 mmol) at 0°C and the reaction mixture was stirred for 10 minutes. Subsequently, iodomethane (CH3I, 1 mL, 16 mmol) was added and the reaction continued to be stirred for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (30 mL) and extracted with ethyl acetate (3 x 30 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, 10% v/v) to give the title compound (1.1 g, 94% yield) as a white solid. LCMS: 203 [M+2]+. 1H NMR (400 MHz, DMSO-d6) δ 2.99 (s, 6H), 6.61 (d, J = 9.6 Hz, 1H), 7.62 (dd, J = 9.2, 2.8 Hz, 1H), 8.12 (d, J = 2.4 Hz, 1H).

References

[1] Patent: WO2011/130628, 2011, A1. Location in patent: Page/Page column 206
[2] Patent: US2013/102595, 2013, A1. Location in patent: Paragraph 0485; 0486
[3] Patent: JP2015/187145, 2015, A. Location in patent: Paragraph 0418

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