2-Chloropropiophenone Chemical Properties

Melting point:

213-214 °C

Boiling point:

80 °C(Press: 0.3 Torr)

Density 

1.560 g/cm3(Temp: 25 °C)

refractive index 

1.5430-1.5470

form 

clear liquid

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C9H9ClO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,1H3

InChIKey

AXCPQHPNAZONTH-UHFFFAOYSA-N

SMILES

C(C1=CC=CC=C1)(=O)C(Cl)C

CAS DataBase Reference

6084-17-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2914790090

2-Chloropropiophenone Usage And Synthesis

Synthesis Reference(s)

The Journal of Organic Chemistry, 28, p. 630, 1963 DOI: 10.1021/jo01038a007

Synthesis

Step 1: Preparation of allylsilane ether: add phenylacetone (1 g, 8 mmol) to a 50 mL two-necked flask, and cool the solution to 0 ?? under nitrogen protection, then add 10 mL of anhydrous THF solution, then add lithium diisopropylammonium (2 mol/L, 4.2 mL) drop by drop to it, and when the addition is completed, remove the ice-water mixture used for cooling, and stir the solution at room temperature for 1 h. When the solution turns yellow, add trimethylchlorosilane (1.04 g, 9.6 mmol) to it drop by drop, and then add the lithium chlorotrimethylsilane (1.04 g, 9.6 mmol) to it. When the solution turned yellow, the reaction mixture was cooled to 0 ?? again, to which trimethylchlorosilane (1.04 g, 9.6 mmol) was added dropwise with stirring at room temperature and detected by TLC until the end of the reaction. The solvent was removed by distillation under reduced pressure and the final oily liquid was separated by column chromatography (pure petroleum ether) to give product 1a (1.3 g, yield: 84%).

Step 2: Preparation of α-chloropropiophenone: To a 50 mL two-necked vial was added iodobenzene diacetate (2a) (0.244 g, 0.75 mmol) protected by nitrogen, then phenylpropiophenone enol silane (1a) (0.096 g, 0.5 mmol) and trimethylchlorosilane (3a) (0.108 g, 1 mmol) of MeCN (5 mL) solution was added to the system. The reaction system was allowed to stir at room temperature and detected by TLC until the reaction was complete. After removal of the solvent by distillation under reduced pressure, the residue was separated by column chromatography [V(petroleum ether):V(ethyl acetate) = 10:1]. Final isolation gave the product 4l (α-chloropropiophenone) as a colorless liquid in 84% yield.

2-Chloropropiophenone(6084-17-9)Related Product Information

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