6-(Trifluoromethyl)-1-indanone Chemical Properties

Boiling point:

76-78 °C/0.2 mmHg

Density 

1.321 g/mL at 25 °C

refractive index 

n20/D 1.496

Flash point:

110 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Light yellow to brown Solid-Liquid Mixture

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43

Safety Statements 

36/37

WGK Germany 

3

HS Code 

2914790090

6-(Trifluoromethyl)-1-indanone Usage And Synthesis

Uses

6-(Trifluoromethyl)-1-indanone is a useful research chemical compound used as a reactant in the enantioselective synthesis of homoallylic azides and nitriles.

Synthesis

Step D: Synthesis of 6-(trifluoromethyl)-1-indanone To a mixed solution of 3-(2-bromo-4-(trifluoromethyl)phenyl)propanoic acid (6.40 g, 21.5 mmol) in THF (300 mL) and hexane (80 mL) was slowly added a 2.5 M n-butyllithium hexane solution (19 mL) at -78°C. The reaction mixture was stirred at this temperature for 15 minutes and then carefully poured into 2N HCl solution (150 mL) to terminate the reaction. The organic and aqueous layers were separated and the aqueous layer was extracted with ether. All organic layers were combined, washed sequentially with NaHCO3 solution, water and brine, dried over anhydrous MgSO4 and concentrated. Purification by silica gel column chromatography (eluent: 10-20% ethyl acetate in hexane solution) afforded 6-(trifluoromethyl)-1-indanone (2.2 g, yield 51%) as an oil.MS (ESI) calculated value of C10H7F3O(M+H)+: 201.0; measured value: 201.0.

References

[1] Patent: US2005/261310, 2005, A1. Location in patent: Page/Page column 22
[2] Patent: US4132737, 1979, A

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