4-AMINO-3-BROMO-2-METHOXYPYRIDINE Chemical Properties

Melting point:

Oil°

Boiling point:

289.0±35.0 °C(Predicted)

Density 

1.622±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

5.28±0.42(Predicted)

Appearance

yellow solid

InChI

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

InChIKey

FJBMTFANAYFWPT-UHFFFAOYSA-N

SMILES

C1(OC)=NC=CC(N)=C1Br

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

4-AMINO-3-BROMO-2-METHOXYPYRIDINE Usage And Synthesis

Synthesis

Synthesis of 3-bromo-2-methoxypyridin-4-amine (2): 2-Methoxypyridin-4-amine (1, 20.0 g, 161.2 mmol) was dissolved in dichloromethane (200 mL) at 0 °C. To this solution, N-bromosuccinimide (26.6 g, 161.2 mmol) was slowly added, followed by warming the reaction mixture to 30 °C and stirring for 30 min. Upon completion of the reaction, the reaction was quenched with ice-cold water (100 mL) and the reaction mixture was extracted with dichloromethane (300 mL). The organic layers were combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was ground with a solvent mixture of n-pentane and ether to give 3-bromo-2-methoxypyridin-4-amine (2) as a yellow solid. Yield: 30.0 g, 92% yield; MS (ESI) m/z 203.09 [M + 1]+.

References

[1] Patent: US2017/145026, 2017, A1. Location in patent: Paragraph 0719; 0720
[2] Patent: WO2016/124508, 2016, A1. Location in patent: Page/Page column 60; 61
[3] Patent: CN107151240, 2017, A. Location in patent: Paragraph 0498; 0499; 0500
[4] Patent: US2018/244667, 2018, A1. Location in patent: Paragraph 0106
[5] Tetrahedron, 2008, vol. 64, # 12, p. 2772 - 2782