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

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

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

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.

Alternating current electrolysis for organic electrosynthesis: Trifluoromethylation of (hetero)arenes

Paired electrolysis has a limited reaction scope for organic synthesis because it is often not compatible with reactions involving short-lived intermediates. We addressed this limitation using alternating current electrolysis (ACE). Using trifluoromethyla

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.

Photoinduced Cobalt(III)?Trifluoromethyl Bond Activation Enables Arene C?H Trifluoromethylation

Visible-light capture activates a thermodynamically inert CoIII?CF3 bond for direct C?H trifluoromethylation of arenes and heteroarenes. New trifluoromethylcobalt(III) complexes supported by a redox-active [OCO] pincer ligand were prepared. Coordinating solvents, such as MeCN, afford green, quasi-octahedral [(SOCO)CoIII(CF3)(MeCN)2] (2), but in non-coordinating solvents the complex is red, square pyramidal [(SOCO)CoIII(CF3)(MeCN)] (3). Both are thermally stable, and 2 is stable in light. But exposure of 3 to low-energy light results in facile homolysis of the CoIII?CF3 bond, releasing .CF3 radical, which is efficiently trapped by TEMPO. or (hetero)arenes. The homolytic aromatic substitution reactions do not require a sacrificial or substrate-derived oxidant because the CoII by-product of CoIII?CF3 homolysis produces H2. The photophysical properties of 2 and 3 provide a rationale for the disparate light stability.

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.

Silver-catalysed trifluoromethylation of arenes at room temperature

A variety of heteroarenes and electron rich arenes can be trifluoromethylated at room temperature with TMSCF3, catalytic silver and PhI(OAc)2.

AMINOETHANOL DERIVATIVES

The present invention provides a pharmaceutical agent having cholesteryl ester transfer protein inhibitory action and useful as a blood lipid lowering agent and the like. The present invention relates to a compound represented by the formula wherein Ar1 is an aromatic ring group optionally having substituents, Ar2 is an aromatic ring group having substituents, OR'' is an optionally protected hydroxyl group, R is an acyl group, R' is a hydrogen atom or a hydrocarbon group optionally having substituents, or a salt thereof, and a pharmaceutical composition containing a compound of the formula (I) or a salt thereof or a prodrug thereof.

Reaction of ethyl 4,4,4-trifluoroacetoacetate enolate with 3-bromo-1,1,1-trifluoroacetone: Synthesis of 2,4-bis (trifluoromethyl) furan

The potassium enolate of ethyl 4,4,4-trifluoroacetoacetate 1 reacts with 3-bromo-1,1,1-trifluoroacetone 2 in DMSO solution to yield three products. Ethyl 2,4-bis(trifluoromethyl)-4-hydroxydihydro-3-furoate 3 is generated via C-acylation. The hydrated trifluoromethyl ketone 4 is formed by O-alkylation and 4 reacts further with 2 to give the di-O-alkylated ketone hydrate 5. Compound 3 undergoes dehydration to the furan derivative 6 on reaction with Ac2O-ZnCl2.