3-Amino-2-bromo-5-fluoropyridine Chemical Properties

Melting point:

114-116 °C

Boiling point:

273.6±35.0 °C(Predicted)

Density 

1.813±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

-0.50±0.10(Predicted)

color 

White to off-white

InChI

InChI=1S/C5H4BrFN2/c6-5-4(8)1-3(7)2-9-5/h1-2H,8H2

InChIKey

QUZAKZBKMMUARE-UHFFFAOYSA-N

SMILES

C1(Br)=NC=C(F)C=C1N

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

2933399990

3-Amino-2-bromo-5-fluoropyridine Usage And Synthesis

Description

3-Amino-2-bromo-5-fluoropyridine is a polyhalogenated pyridine with the chemical formula C5H4BrFN2. The compound has three functional groups: amino, bromine and fluorine, which change its reactivity. It is a crucial compound that could be used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.

Synthesis

Step 1: A suspension of 2-bromo-5-fluoro-3-nitropyridine (4.42 g, 20 mmol) with stannous chloride (SnCl2, 22.56 g, 100 mmol) in ethanol (EtOH, 40 mL) and concentrated hydrochloric acid (HCl, 40 mL) was heated to 60°C and reacted for 1 hour. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. To the residue was added ethyl acetate (EtOAc, 100 mL) and saturated aqueous sodium bicarbonate (NaHCO3). The mixture was filtered through diatomaceous earth (Celite) and extracted with ethyl acetate (100 mL x 3). The organic layers were combined, washed sequentially with saturated sodium bicarbonate solution, water and brine, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give 3.1 g of 2-bromo-5-fluoropyridin-3-amine as a brown solid (80% yield). Mass spectrum (ESI): m/z = 191.1 [M + 1]+.

References

[1] Patent: WO2013/92940, 2013, A1. Location in patent: Page/Page column 50; 51

3-Amino-2-bromo-5-fluoropyridine(884495-03-8)Related Product Information

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