5-BROMO-3-METHOXYPYRIDIN-2-AMINE Chemical Properties

Melting point:

78-82℃

Boiling point:

254℃

Density 

1.622

Flash point:

107℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

5.93±0.10(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C6H7BrN2O/c1-10-5-2-4(7)3-9-6(5)8/h2-3H,1H3,(H2,8,9)

InChIKey

NFBIWMFMHLPVLT-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C=C1OC

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

5-BROMO-3-METHOXYPYRIDIN-2-AMINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-amino-3-methoxy-5-bromopyridine from 2-amino-3-methoxypyridine: To a 2000 mL Erlenmeyer flask was added 10% sulfuric acid solution (800 mL). 2-Amino-3-methoxypyridine (25.80 g, 206 mmol) was added at room temperature while stirring. After the solution was clarified, it was cooled to about 3°C in an ice/water bath. Subsequently, bromine (10.8 mL, 210 mmol) was slowly added to the mixture in acetic acid at 0°C. Upon completion of the reaction, the solid product was collected by filtration, washed twice (30 mL each) with cold water and dried to give 39.0 g of crude product. The crude product was suspended in ethyl acetate (500 mL) with vigorous stirring for 0.5 h and then filtered through Celite. The black solid was washed twice with ethyl acetate, and the filtrates were combined and washed sequentially with 10% sodium thiosulfate solution (100 mL) and saturated brine, and finally dried over anhydrous sodium sulfate. The mixture was concentrated to give 29.0 g (68.3% yield) of 2-amino-3-methoxy-5-bromopyridine as a yellow solid. The product was confirmed by 1H NMR (300 MHz, CDCl3): δ 7.71 (d, J = 2.1 Hz, 1H), 7.01 (d, J = 2.1 Hz, 1H), 4.69 (br s, 2H), 3.84 (s, 3H).LC-MS (m/z): 204.9 ([M+H]+).

References

[1] Patent: US2011/81316, 2011, A1. Location in patent: Page/Page column 14
[2] Patent: WO2010/96389, 2010, A1. Location in patent: Page/Page column 45-46; 48
[3] Patent: WO2010/135014, 2010, A1. Location in patent: Page/Page column 53-55
[4] Patent: WO2017/76931, 2017, A1. Location in patent: Page/Page column 20
[5] Patent: WO2010/100127, 2010, A1. Location in patent: Page/Page column 71-72

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