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2-(Trifluoromethyl)benzophenone

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2-(Trifluoromethyl)benzophenone Basic information
Application
Product Name:2-(Trifluoromethyl)benzophenone
Synonyms:Methanone, phenyl[2-(trifluoromethyl)phenyl]-;o-Trifluoromethylbenzophenone;Phenyl[2-(trifluoromethyl)phenyl]methanone;2-(TRIFLUOROMETHYL)BENZOPHENONE 99%;2-(Trifluoromethyl)benzophenone98%;(2-(trifluoromethyl)phenyl)(phenyl)methanone;2-(Trifluoromethyl)benzophenone
CAS:727-99-1
MF:C14H9F3O
MW:250.22
EINECS:211-972-2
Product Categories:Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Fluorine series;Benzene series;C13 to C14;Carbonyl Compounds;Ketones
Mol File:727-99-1.mol
2-(Trifluoromethyl)benzophenone Structure
2-(Trifluoromethyl)benzophenone Chemical Properties
Melting point 60-62 °C
Boiling point 175-178 °C(Press: 31 Torr)
density 1.2778 (estimate)
storage temp. Sealed in dry,Room Temperature
form solid
color Off-white
BRN 2375025
InChI1S/C14H9F3O/c15-14(16,17)12-9-5-4-8-11(12)13(18)10-6-2-1-3-7-10/h1-9H
InChIKeyJXIWJBWMQXDALU-UHFFFAOYSA-N
SMILESFC(F)(F)c1ccccc1C(=O)c2ccccc2
CAS DataBase Reference727-99-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 37/39-26-36
WGK Germany 3
HazardClass IRRITANT
HS Code 2914790090
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
ACROS English
ALFA English
2-(Trifluoromethyl)benzophenone Usage And Synthesis
Application2-(trifluoromethyl)benzophenone is an ultraviolet absorber and a pharmaceutical and pesticide chemical intermediate with wide applications in these fields. It can also be used in the synthesis of fluorine-containing polymers. Furthermore, 2-(trifluoromethyl)benzophenone is an important pharmaceutical intermediate.
Chemical Propertiesyellow crystal powde
UsesAssymmetric reduction of 2-(trifluoromethyl)benzophenone by lithium aluminium hydride treated with (S)-(+) or (R)-(−)-2 (2-iso-indolinyl)butan-1-ol has been investigated.
Synthesis Reference(s)Tetrahedron Letters, 35, p. 1047, 1994 DOI: 10.1016/S0040-4039(00)79962-X
General DescriptionAssymmetric reduction of 2-(trifluoromethyl)benzophenone by lithium aluminium hydride treated with (S)-(+) or (R)-()-2 (2-iso-indolinyl)butan-1-ol has been investigated.
Synthesis

The literature Bull.Soc.Chim.France 1962, 587-93 mentions the preparation of 2-(trifluoromethyl)phenyl ketone by the Grignard reaction using the Grignard reagents m-trifluoromethylphenylmagnesium bromide and m-trifluoromethylbenzonitrile feedstock, but the Grignard reaction is difficult to industrialize.

The raw material 10 g of 2-(trifluoromethyl)benzyl methane, 100 g of solvent chloroform and 0.2 g of catalyst phosphorus pentachloride were mixed, and then 7 g of chlorine gas was passed under 100 w incandescent light, 60 reflux for 20 hours, and the reaction process was tracked by GC and NMR; 

End of the reaction, cooling, adding water, extraction with chloroform, stratification, the oil layer was concentrated to get the intermediate colorless oil 2-(trifluoromethyl)phenyl dichloromethane; 

Intermediate 2-(trifluoromethyl)phenyl dichloromethane, 30 grams of water, 12 grams of acetonitrile and 3 grams of sodium hydroxide were mixed and refluxed for 4 hours, cooled and filtered to obtain the crude product, which was recrystallized with ethanol to obtain 7.8 grams of the target product 2-(trifluoromethyl)phenyl ketone as white crystals.  

Yield of the above two steps by recrystallization was about: 74.5%.

2-(Trifluoromethyl)benzophenone Preparation Products And Raw materials
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