1-(2-CHLORO-PYRIDIN-4-YL)-ETHANONE Chemical Properties

Melting point:

36.5 °C

Boiling point:

270.2±25.0 °C(Predicted)

Density 

1.233±0.06 g/cm3(Predicted)

Flash point:

>110℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

-1.55±0.10(Predicted)

color 

Off white to brown

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT-HARMFUL

HazardClass 

6.1

HS Code 

2933399990

1-(2-CHLORO-PYRIDIN-4-YL)-ETHANONE Usage And Synthesis

Uses

1-(2-Chloro-4-pyridinyl)ethanone is used for the synthesis of pyrimidine derivatives as hSMG-1 inhibitors in the treatment of cancer.

Synthesis

Step 2: Synthesis of 1-(2-chloropyridin-4-yl)ethanone To a solution of 2-chloro-N-methoxy-N-methylisonicotinamide (10.0 g, 50 mmol) in anhydrous tetrahydrofuran (50 mL) was slowly added 3M methylmagnesium bromide solution in tetrahydrofuran (50 mL, 150 mmol) at 0 °C, keeping stirring. After addition, the reaction mixture was gradually warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution, followed by extraction of the organic phase with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford 1-(2-chloropyridin-4-yl)ethanone (7.5 g, 96% yield). Mass spectrometric analysis (ESI) showed m/z: 156.0 [M + H]+.

References

[1] Patent: EP2952510, 2015, A1. Location in patent: Paragraph 0106
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6636 - 6641,6
[3] Patent: WO2016/97351, 2016, A1. Location in patent: Page/Page column 11-12
[4] Patent: WO2004/78682, 2004, A2. Location in patent: Page 17-18
[5] Patent: US2012/225876, 2012, A1. Location in patent: Page/Page column 50

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