1-(5-BROMO-PYRIDIN-2-YL)-ETHANONE Chemical Properties

Melting point:

112 °C

Boiling point:

257.2±25.0 °C(Predicted)

Density 

1.534±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Sparingly)

form 

Solid

pka

0?+-.0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C7H6BrNO/c1-5(10)7-3-2-6(8)4-9-7/h2-4H,1H3

InChIKey

IDZRAUUUHXQGKC-UHFFFAOYSA-N

SMILES

C(=O)(C1=NC=C(Br)C=C1)C

Safety Information

HS Code 

2933399990

1-(5-BROMO-PYRIDIN-2-YL)-ETHANONE Usage And Synthesis

Uses

1-(5-Bromo-2-pyridyl)ethanone is a reagent used to synthesize substituted pyridin-3-yl)phenyloxazolidinones as antibacterial agents with reduced activity against monoamine oxidase A.

Synthesis

2,5-Dibromopyridine (I-1-1) 8 g (33.7 mmol) was stirred with 337 mL of toluene at -40 °C in a nitrogen atmosphere. After stirring for 40 min, 21.4 mL (1.02 eq.) of a hexane solution of 1.6 M n-butyllithium was added slowly and dropwise to the reaction system, followed by 9.38 mL (3.0 eq.) of N,N-dimethylacetamide (DMAc). The reaction mixture was stirred and gradually warmed to 20 °C. Upon completion of the reaction, the reaction was quenched by the addition of saturated aqueous ammonium chloride, followed by extraction and liquid-liquid separation. The organic phase was purified by silica gel column chromatography to afford the target product 2-acetyl-5-bromopyridine (Compound I-1-2) 6.74 g in 100% yield as a white solid.

References

[1] Patent: JP2016/56276, 2016, A. Location in patent: Paragraph 0111; 0112
[2] Tetrahedron, 2008, vol. 64, # 17, p. 3794 - 3801
[3] Dalton Transactions, 2011, vol. 40, # 29, p. 7534 - 7540
[4] Journal of the American Chemical Society, 2016, vol. 138, # 38, p. 12643 - 12647
[5] Patent: WO2015/27021, 2015, A1. Location in patent: Page/Page column 78

1-(5-BROMO-PYRIDIN-2-YL)-ETHANONE(214701-49-2)Related Product Information

• 2-Acetyl-3-fluoropyridine
• 2-Acetylpyridine
• 1-(2-BROMO-PYRIDIN-3-YL)-ETHANONE
• 1-(6-BROMO-PYRIDIN-3-YL)-ETHANONE
• 3-ACETYL-5-BROMOPYRIDINE
• 2-BROMO-1-(6-BROMO-PYRIDIN-2-YL)-ETHANONE
• BIS(5-BROMO-2-PYRIDINYL)METHANONE
• 1-(5-BROMO-PYRIDIN-2-YL)-ETHANONE
• (5-BROMO-PYRIDIN-2-YL)-PHENYL-METHANONE
• 1-(5-BROMO-PYRIDIN-2-YL)-2,2,2-TRIFLUORO-ETHANONE
• ethyl 3-(5-bromopyridin-2-yl)-3-oxopropanoate
• 1-(3,5-DIBROMO-PYRIDIN-2-YL)-ETHANONE
• 7-Bromo-4-oxo-1,4-dihydro-[1,5]naphthyridine-2-carboxylic acid ethyl ester