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387-89-3

387-89-3 Structure

387-89-3 Structure
IdentificationBack Directory
[Name]

2-(TRIFLUOROACETYL)CYCLOHEXANONE
[CAS]

387-89-3
[Synonyms]

AKOS B029513
2-(TRIFLUOROACETYL)CYCLOHEXANONE
2-(trifluoroacetyl)cyclohexan-1-one
2-(2,2,2-trifluoroacetyl)cyclohexanone
Cyclohexanone, 2-(2,2,2-trifluoroacetyl)-
2-(2,2,2-trifluoroethanoyl)cyclohexan-1-one
[Molecular Formula]

C8H9F3O2
[MDL Number]

MFCD07779548
[MOL File]

387-89-3.mol
[Molecular Weight]

194.15
Chemical PropertiesBack Directory
[Boiling point ]

219.3±40.0 °C(Predicted)
[density ]

1.289±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[form ]

liquid
[pka]

7.80±0.20(Predicted)
[color ]

Light yellow
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2914790090
Hazard InformationBack Directory
[Uses]

2-(2,2,2-Trifluoroacetyl)cyclohexanone is a useful reactant for the synthesis of fluorinated 1-?desazapurines.
[Synthesis]

Ethyl trifluoroacetate

383-63-1

Cyclohexanone

108-94-1

2-(TRIFLUOROACETYL)CYCLOHEXANONE

387-89-3

GENERAL PROCEDURE: In a dry Schlenk tube, NaH (6.0 mmol) was stirred with ethyl trifluoroacetate (6.0 mmol) in THF (5 mL) for 10 minutes at room temperature under argon protection. Subsequently, a THF (5 mL) solution of cyclohexanone (5.0 mmol) was added dropwise to the above mixture at 0 °C and under argon protection. The reaction mixture was stirred at the set temperature for 2-6 h. After that, it was cooled to 0 °C again and the reaction was quenched with 6 mL of 1 mol/L HCl solution. After continued stirring for 15 min, the reaction mixture was neutralized with saturated NaHCO3 solution. After conventional post-treatment, the residue was purified by silica gel column chromatography to afford the target product 2-(trifluoroacetyl)cyclohexanone.

[References]

[1] Tetrahedron, 2014, vol. 70, # 31, p. 4668 - 4674
[2] Magnetic Resonance in Chemistry, 1993, vol. 31, # 4, p. 323 - 328
[3] Journal of the American Chemical Society, 1953, vol. 75, p. 4753
[4] New Journal of Chemistry, 2007, vol. 31, # 6, p. 936 - 946
[5] RSC Advances, 2016, vol. 6, # 46, p. 40277 - 40286
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