3',5'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE Chemical Properties

Boiling point:

265℃

Density 

1.506

refractive index 

1.4980 to 1.5020

Flash point:

114℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless

InChI

InChI=1S/C8H3Cl2F3O/c9-5-1-4(2-6(10)3-5)7(14)8(11,12)13/h1-3H

InChIKey

DZDSQRPDUCSOQV-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

130336-16-2

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2914790090

3',5'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE Usage And Synthesis

Uses

3'',5''-Dichloro-2,2,2-trifluoroacetophenone is a reagent used for enantioselective preparation of benzazephinoindoles bearing trifluoromethylated quaternary stereocenters catalyzed by chiral spirocyclic phosphoric acids

Synthesis

Under nitrogen protection, tert-butyllithium (1.3 M in pentane, 17.8 mL, 23.2 mmol) was slowly added dropwise to a solution of 3,5-dichloro-1-bromobenzene (5.0 g, 22.1 mmol) in tetrahydrofuran (50 mL) over a period of 30 min, followed by continuing the reaction for 2 h at -78 °C. Upon completion of the reaction, trifluoroacetic anhydride (2.56 g, 12.2 mmol) was slowly added dropwise to the reaction mixture and stirring was continued for 2 hours at -78 °C. The cooling bath was removed and the reaction mixture was allowed to warm slowly to room temperature and stirring was continued at room temperature for 2.5 hours. When the reaction was terminated, saturated ammonium chloride solution (50 mL) was added. The reaction mixture was extracted with ether (3 x 50 mL) and the organic phases were combined and washed with saturated brine (20 mL x 2). The organic phase was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, and purified by distillation under reduced pressure to give the colorless transparent liquid 3',5'-dichloro-2,2,2-trifluoroacetophenone (2.58 g, 48% yield).

References

[1] Patent: CN107353189, 2017, A. Location in patent: Paragraph 0019; 0023
[2] Bulletin of the Chemical Society of Japan, 1997, vol. 70, # 12, p. 3081 - 3090

3',5'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE(130336-16-2)Related Product Information

• 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid
• Fluralaner Impurity 4
• Fluralaner
• Malononitrile
• Lithium trifluoromethanesulfonate
• Copper(II) chloride dihydrate
• SODIUM METHACRYLATE
• Copper(II) sulfate pentahydrate
• Benzoyl chloride
• Chalcone
• Dichloroethane
• 2',5'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE
• 2',4'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE
• 2,6-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE
• 2',3'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE
• 3',4'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE
• 3'-CHLORO-2,2,2-TRIFLUOROACETOPHENONE
• 3',5'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE