685892-24-4

Basic information

• Product Name: 3,5-BIS(TRIFLUOROMETHYL)THIOANISOLE
• Synonyms: 1-METHYLSULFANYL-3,5-BIS-TRIFLUOROMETHYL-BENZENE;3,5-BIS(TRIFLUOROMETHYL)THIOANISOLE
• CAS NO: 685892-24-4
• Molecular Formula: C₉H₆F₆S
• Molecular Weight: 260.2
• Mol File: 685892-24-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5-BIS(TRIFLUOROMETHYL)THIOANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-BIS(TRIFLUOROMETHYL)THIOANISOLE(685892-24-4)
• EPA Substance Registry System: 3,5-BIS(TRIFLUOROMETHYL)THIOANISOLE(685892-24-4)

Safety Data

• Hazardous Substances Data: 685892-24-4(Hazardous Substances Data)

Upstream product

• 124-38-9 carbon dioxide 
• 130783-02-7 3,5-bis(trifluoromethyl)thiophenol 

Downstream Products

• 349-58-6 3,5-bis-(trifluoromethyl)phenol 
• 2548-47-2 2,3-diphenyl-1,3-butadiene 
• 4210-04-2 3,5-bis(trifluoromethyl)phenyl methyl sulfone 

Relevant articles and documents

Reduction of CO2 with NaBH4/I2 for the Conversion of Thiophenols to Aryl Methyl Sulfides

We report a tandem reaction to realize reduction of carbon dioxide with thiophenols to generate aryl methyl sulfides under the NaBH4/I2 system with 18-crown-6 as the solvent. Thiophenols bearing electron-donating and electron-withdrawing groups are feasible in this reaction. Controlled experiment results indicate that 18-crown-6 plays a critical role in six-electron reduction of carbon dioxide.

3,5-Bis(trifluoromethyl)phenyl sulfones in the direct Julia-Kocienski olefination

3,5-Bis(trifluoromethyl)phenyl (BTFP) sulfones 7 have been employed in the Julia-Kocienski olefination reaction with carbonyl compounds. Sulfones 7 are readily prepared in high yields (64-97%) from commercially available 3,5-bis(trifluoromethyl)thiophenol through an alkylation/oxidation two-step sequence. The stability of metalated BTFP sulfones has been studied and compared with heteroaryl benzothiazol-2-yl (BT), 1-phenyl-1H-tetrazol-5-yl (PT), and 1-tert-butyl-1H-tetrazol-5-yl (TBT) sulfones 9-11 under different reaction conditions. The Julia-Kocienski olefination between alkyl BTFP sulfones 7 and a wide variety of aldehydes affords the corresponding 1,2-disubstituted alkenes and dienes in good yields and stereoselectivities. This one-pot protocol can be performed using KOH at room temperature or the phosphazene bases P2-Et and P4-t-Bu at -78 °C or rt and has been successfully used in a high-yielding and stereoselective synthesis of various methoxylated stilbenes such as trimethylated resveratrol. These new reaction conditions for the Julia-Kocienski olefination reaction have been also studied with BT, PT, and TBT sulfones, giving poorer results. Methylenation of aliphatic and aromatic aldehydes, ketones, and 1,2-dicarbonyl compounds is carried out through the modified Julia olefination using BTFP methyl sulfone 7d to give terminal alkenes and dienes. Mechanistic studies of the olefination reaction between benzyl BTFP sulfone 7a and aromatic aldehydes performed by KOH-induced Smiles rearrangement of stereodefined syn- and anit-β-hydroxyalkyl BTFP sulfones indicate that the stereocontrol of the reaction is determined in the elimination step. 2005 American Chemical Society.