5-Acetyl-2-bromopyridine Chemical Properties

Melting point:

124-128 °C (lit.)

Boiling point:

304.7±27.0 °C(Predicted)

Density 

1.534±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-1.01±0.10(Predicted)

color 

Light orange to Yellow to Green

InChI

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

InChIKey

MUKKGHQBUKOMTD-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=C(Br)N=C1)C

CAS DataBase Reference

139042-59-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

5-Acetyl-2-bromopyridine Usage And Synthesis

Uses

5-Acetyl-2-bromopyridine is used as biochemical reagent and organic intermediate.

Synthesis

Step 1: Synthesis of 1-(6-bromopyridin-3-yl)ethanone To a stirred solution of 2,5-dibromopyridine (1.0 g, 4.219 mmol) in ether (10 mL) was slowly added n-butyllithium (2.0 mL, 5.0 mmol, 2.5 M hexane solution) at -78 °C and the reaction was carried out under nitrogen protection. After keeping stirring at -78 °C for 1 h, N,N-dimethylacetamide (0.58 g, 6.3 mmol) was added dropwise and stirring was continued at -78 °C for 4 h. The reaction was carried out under nitrogen protection. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction was quenched with ice water and subsequently partitioned between saturated ammonium chloride (NH4Cl) solution and ethyl acetate (EtOAc). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1-(6-bromopyridin-3-yl)ethanone (0.4 g, 47% yield) as a yellow solid. Mass spectrometry (MS) showed a molecular ion peak m/z 200.1 [M++1].

References

[1] Molecules, 2008, vol. 13, # 4, p. 818 - 830
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6763 - 6770
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 11, p. 3860 - 3874
[4] Patent: US2017/291894, 2017, A1. Location in patent: Paragraph 0428
[5] Chemische Berichte, 1992, vol. 125, # 5, p. 1169 - 1190

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