3-ACETYL-2-CHLOROPYRIDINE Chemical Properties

Boiling point:

114°C/15mmHg(lit.)

Density 

1.233±0.06 g/cm3(Predicted)

refractive index 

1.5440-1.5480

Flash point:

>110℃

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

pka

-1.65±0.10(Predicted)

color 

Colorless to Brown

InChI

InChI=1S/C7H6ClNO/c1-5(10)6-3-2-4-9-7(6)8/h2-4H,1H3

InChIKey

WIWIOUAFBHZLNQ-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=CN=C1Cl)C

CAS DataBase Reference

55676-21-6

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

3-ACETYL-2-CHLOROPYRIDINE Usage And Synthesis

Uses

3-Acetyl-2-chloropyridine is a reagent used in the synthesis of Volitinib, a highly potent and selective mesenchymal-epithelial transition factor (c-Met) inhibitor as an anti-cancer agent.

Synthesis

Step 2: Synthesis of 1-(2-chloropyridin-3-yl)ethanone 1-(2-Chloropyridin-3-yl)ethanol (10 g, 0.0635 mol) was dissolved in anhydrous acetone (200 mL), transferred to a 1-liter flask and the reaction was carried out under argon protection. The reaction mixture was cooled to -30 °C, followed by slow addition of pure crushed chromic anhydride (19 g, 0.19 mol). The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, 2-propanol (100 mL) was added to quench the reaction, followed by adjusting the pH with aqueous sodium bicarbonate to 8. The reaction mixture was filtered and the solid was washed with chloroform. The organic and aqueous layers were separated and the aqueous layer was further extracted with chloroform (2 x 100 mL). All organic phases were combined and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure to give the crude 1-(2-chloropyridin-3-yl)ethanone as an oil. The crude product was purified by column chromatography to afford the pure 1-(2-chloropyridin-3-yl)ethanone (8 g, 81% yield). * 1H NMR (CDCl3) δ 8.44 (dd, J = 5 and 2 Hz, 1H), 7.91 (dd, J = 7.5 and 2 Hz, 1H), 7.34 (dd, J = 7.5 and 5 Hz, 1H), 2.68 (s, 3H).

References

[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 9, p. 2409 - 2415
[2] Patent: US2006/47126, 2006, A1. Location in patent: Page/Page column 30
[3] Patent: WO2011/5759, 2011, A2. Location in patent: Page/Page column 77
[4] Patent: WO2011/84486, 2011, A1. Location in patent: Page/Page column 106; 110-111
[5] Patent: US2013/296302, 2013, A1. Location in patent: Paragraph 0494

3-ACETYL-2-CHLOROPYRIDINE(55676-21-6)Related Product Information

• 5-Acetyl-2-chloropyridine
• 4-ACETYL-2-CHLOROPYRIDINE
• 2-ACETYL-3-CHLOROPYRIDINE
• 3-Acetylpyridine
• 2-CHLORO-3-(5-ETHOXYCARBONYL-2-THENOYL)PYRIDINE
• ETHYL 4-(2-CHLORO-3-PYRIDYL)-4-OXOBUTYRATE
• 2-CHLORO-3-(3-ETHOXYCARBONYLBENZOYL)PYRIDINE
• ETHYL 3-(2,6-DICHLORO-5-FLUOROPYRIDIN-3-YL)-3-OXOPROPANOATE
• 4-(2-CHLORO-3-PYRIDYL)-4-OXOBUTYRONITRILE
• ETHYL 5-(2-CHLORO-3-PYRIDYL)-5-OXOVALERATE
• 2-CHLORO-3-(3-METHYL-2-THENOYL)PYRIDINE
• 2-CHLORO-3-(2-CYANOBENZOYL)PYRIDINE
• ETHYL 8-(2-CHLORO-3-PYRIDYL)-8-OXOOCTANOATE
• 2-CHLORO-3-(2-THIAZOLYLCARBONYL)PYRIDINE
• 2-CHLORO-3-(5-ETHOXYCARBONYL-2-FUROYL)PYRIDINE
• 2-CHLORO-3-(4-ETHOXYCARBONYLBENZOYL)PYRIDINE
• ETHYL 7-(2-CHLORO-3-PYRIDYL)-7-OXOHEPTANOATE
• ETHYL 6-(2-CHLORO-3-PYRIDYL)-6-OXOHEXANOATE