Chemical Properties
Liquid. Boiling point 123°C (98 kPa, decomposition), 55°C (2.13 kPa), relative density 1.068 (23/4°C), refractive index 1.4284 (23°C).
Uses
4-Chloro-2-butanone acts as a reagent for the preparation of pyrrolopyrazine derivatives as selective spleen tyrosine kinase inhibitors.
Application
4-Chloro-2-butanone is a reagent for Robinson annulation; often interchangeable with methyl vinyl ketone and the corresponding Mannich base 4-dialkylamino-2-butanone.
Synthesis
General procedure for the synthesis of β-chlorobutanone from 4-hydroxy-2-butanone: 4-hydroxy-2-butanone (0.881 g, 10 mmol), dichloromethane (2 ml), and thionyl chloride (1.46 ml, 20 mmol) were added in a reaction flask and the reaction was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by rotary evaporator and the residue was dried with a stream of nitrogen to give 2-chlorobutan-2-one (1.06 g). The product was characterized by 1H-NMR (400 MHz, DMSO-d6): δ 2.12 (s, 3H), 2.94 (t, 2H), 3.74 (t, 2H).
References
[1] Angewandte Chemie - International Edition, 2012, vol. 51, # 27, p. 6713 - 6716
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1936, vol. 202, p. 1687
[3] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 909
[4] Chem. Zentralbl., 1939, vol. 110, # I, p. 4953
[5] Patent: WO2015/169999, 2015, A1. Location in patent: Page/Page column 63
