3-Acetyl-2-bromopyridine Chemical Properties

Boiling point:

115 °C(Press: 7 Torr)

Density 

1.552 g/mL at 25 °C

refractive index 

n20/D1.572

Flash point:

>110℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

liquid

pka

-1.01±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

1

HS Code 

2933399990

3-Acetyl-2-bromopyridine Usage And Synthesis

Uses

3-Acetyl-2-bromopyridine is a chemical reagent used in nonquaternary reactivators of GF-inhibited human acetylcholinesterase. Also used in the synthesis of HIV-1 reverse transriptase inhibitors.

Synthesis

GENERAL METHOD: CrO3 (33.1 g, 0.331 mol) was slowly added in small portions to a solution of 1-(2-bromopyridin-3-yl)ethanol (30.5 g, 0.133 mol) in acetone (350 mL). The reaction mixture was stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure and hexane (1 L) was added, followed by a solution of NaOH (26.5 g, 0.662 mol) in water (150 mL). The mixture was stirred for 30 min. The organic layer was separated, dried with Na2SO4, filtered through a silica gel pad (40 g) and evaporated under reduced pressure.

References

[1] Journal of Chemical Research, Miniprint, 1982, # 10, p. 2863 - 2878
[2] Organic and Biomolecular Chemistry, 2011, vol. 9, # 22, p. 7836 - 7848
[3] Tetrahedron Letters, 2017, vol. 58, # 20, p. 1989 - 1991
[4] Journal of Organic Chemistry, 2017, vol. 82, # 21, p. 11585 - 11593
[5] Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 999 - 1014

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