17515-75-2

Basic information

• Product Name: 2-Methyl-5-(trifluoromethyl)furan
• Synonyms: 2-Methyl-5-(trifluoromethyl)furan;Furan, 2-methyl-5-(trifluoromethyl)-
• CAS NO: 17515-75-2
• Molecular Formula: C₆H₅F₃O
• Molecular Weight: 150.1
• Product Categories: Heterocycles
• Mol File: 17515-75-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 102.172 °C at 760 mmHg
• Flash Point: 15.594 °C
• Appearance: /
• Density: 1.23 g/cm³
• Vapor Pressure: 39.347mmHg at 25°C
• Refractive Index: 1.381
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Methyl-5-(trifluoromethyl)furan(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-5-(trifluoromethyl)furan(17515-75-2)
• EPA Substance Registry System: 2-Methyl-5-(trifluoromethyl)furan(17515-75-2)

Safety Data

• Hazardous Substances Data: 17515-75-2(Hazardous Substances Data)

Usage

Uses

Trifluoromethyl furan derivative.

InChI:InChI=1/C6H5F3O/c1-4-2-3-5(10-4)6(7,8)9/h2-3H,1H3

Upstream product

• 534-22-5 2-methylfuran 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 2314-97-8 iodotrifluoromethane 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 17515-74-1 2-trifluoromethyl-5-methyl-3-furancarboxylic acid 
• 17515-66-1 ethyl 4-oxo-2-(2,2,2-trifluoroacetyl)pentanoate 
• 191598-69-3 1,1,1-trifluoro-2,5-hexanedione 

Downstream Products

• 17515-77-4 2-(bromomethyl)-5-(trifluoromethyl)furan 

Relevant articles and documents

Photoinduced Trifluoromethylation of Arenes and Heteroarenes Catalyzed by High-Valent Nickel Complexes

We describe a series of air-stable NiIII complexes supported by a simple, robust naphthyridine-based ligand. Access to the high-valent oxidation state is enabled by the CF3 ligands on the nickel, while the naphthyridine exhibits either a monodentate or bidentate coordination mode that depends on the oxidation state and sterics, and enables facile aerobic oxidation of NiII to NiIII. These NiIII complexes act as efficient catalysts for photoinduced C(sp2)?H bond trifluoromethylation reactions of (hetero)arenes using versatile synthetic protocols. This blue LED light-mediated catalytic protocol proceeds via a radical pathway and demonstrates potential in the late-stage functionalization of drug analogs.

Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex

While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.

Rapid trifluoromethylation and perfluoroalkylation of five-membered heterocycles by photoredox catalysis in continuous flow

Trifluoromethylated and perfluoroalkylated heterocycles are important building blocks for the synthesis of numerous pharmaceutical products, agrochemicals and are widely applied in material sciences. To date, trifluoromethylated and perfluoroalkylated hetero-aromatic systems can be prepared utilizing visible light photoredox catalysis methodologies in batch. While several limitations are associated with these batch protocols, the application of microflow technology could greatly enhance and intensify these reactions. A simple and straightforward photocatalytic trifluoromethylation and perfluoroalkylation method has been developed in continuous microflow, using commercially available photocatalysts and microflow components. A selection of five-membered hetero-aromatics were successfully trifluoromethylated (12 examples) and perfluoroalkylated (5 examples) within several minutes (8-20 min). Photo workflow: A simple and straightforward photocatalytic method for perfluoroalkylation in continuous flow is developed. A photo-microreactor, constructed from commercially available components, enables accelerated photocatalysis employing [Ru(bpy)3Cl2] as photocatalyst under irradiation by blue LED light. A series of electron-rich hetero-aromatics is successfully trifluoromethylated within 8-16 min. Also, a selection of hetero-aromatics is perfluoroalkylated within 10-20 min.