Trifluoroacetophenone CAS 434-45-7

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  • Appearance: Clear colorless to yellow liquid 
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available

Basic Info of Trifluoroacetophenone

What is Trifluoroacetophenone?

2,2,2-Trifluoroacetophenone is a commonly used chemical reagent, and the commonly used synthetic methods of 2,2,2-trifluoroacetophenone are:

  1. Trifluoroacetic acid is directly reacted with the Grignard reagent of bromobenzene, and the one-step method is directly synthesized. The yield is about 60%. The method has the advantages of simple operation and cheap raw materials. Disadvantages: severe exotherm, low yield.
  2. Under the action of Lewis acid AlCl3 in carbon disulfide solvent at -40°C, trifluoroacetic anhydride and benzene ring undergo Friedel-Crafts acylation reaction, and the yield is about 70%. Advantages of this method: one-step synthesis. Disadvantages: The solvent is highly toxic, AlCl3 is difficult to handle, and the strong acid and alkali used corrode equipment and pollute the environment.
  3. Trifluoromethane gas reacts with benzoate or benzoyl chloride to prepare. Yield 70-80%. Advantages of this method: one-step synthesis of target compounds. The disadvantage is that there are impurities and the yield is not high.

Trifluoroacetophenone Uses

  1. 2,2,2-Trifluoroacetophenone can be used as an organic catalyst for the epoxidation of olefins.
  2. 2,2,2-Trifluoroacetophenone can catalyze the epoxidation of olefin compounds by hydrogen peroxide, avoid the use of heavy metals, and at the same time realize hydrogen peroxide as an oxidant, the source is cheap, the product is clean, and the catalyst is organic, reducing environmental pollution, reaction The substrate is also more extensive and is an ideal catalyst.
  3. 2,2,2-Trifluoroacetophenone can also be used in the oxidation reaction of thioether to prepare nitrogen oxide compounds, etc., and has a relatively wide application prospect.

Preparation of Trifluoroacetophenone

  1. Add 1mol (97.5g) N,O-dimethylhydroxylamine hydrochloride, 1mol (149.1g) triethanolamine, 600ml dichloromethane to the reaction vessel, and stir for 1h at room temperature to obtain free N,O- dimethylhydroxylamine;
  2. Add 150 ml of dichloromethane solution containing 1 mol (210 g) of trifluoroacetic anhydride dropwise to the free N,O-dimethylhydroxylamine obtained in step 2 at 0°C, and after 1.5 h of dropwise addition, keep the temperature to continue the reaction 1.5h, after the reaction was completed, 200ml of water was added to dilute and layered, and the aqueous phase was washed twice with 300ml of dichloromethane solution, and the organic layers were combined. Recover to dryness at -35°C to obtain N,O-dimethyltrifluoroamide to be reacted;
  3. Add 15.8g Mg to the reaction vessel, disperse with 200ml of tetrahydrofuran, drop 50g of bromobenzene (104.9g in total), heat up to 55°C under nitrogen protection for 0.5h, continue to drop the tetrahydrofuran solution of bromobenzene, dropwise After the reaction was continued for 2h, a solution of phenylmagnesium bromide was obtained; at 0°C, the solution of phenylmagnesium bromide was added dropwise to 0.5mol (77.53g, content 95%) N,O-dimethyltrifluoroamide and 200ml In the mixed solution of tetrahydrofuran, the dropwise addition was completed for 2 hours, the reaction was continued at 0°C for 1 hour, and the temperature was raised to room temperature for 6 hours. After the reaction was completed, 100% saturated ammonium chloride solution was added to quench, and 1000ml of water was added for dilution, layering, and the water phase was used. 400ml of dichloromethane solution was extracted twice, the organic layers were combined, washed twice with 400ml of water, dried over anhydrous sodium sulfate, and recovered to dryness at 35-38°C to obtain 2,2,2-trifluoroacetophenone .

Yield in step 1: 98.5%, liquid phase purity 96.8%;

In the second step, the yield was 85.2%, and the liquid phase purity was 95.17%.

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