84355-10-2

Basic information

• Product Name: Benzene, 1,4-dimethoxy-2-(trifluoromethyl)-
• Synonyms: 2-trifluoro-1,4-dimethoxybenzene;2-Trifluoromethyl-1,4-dimethoxybenzene;1,4-dimethoxy-2-trifluoromethylbenzene
• CAS NO: 84355-10-2
• Molecular Formula: C9H9F3O2
• Molecular Weight: 206.164
• Mol File: 84355-10-2.mol

Chemical Properties

• Boiling Point: 227.6±40.0 °C(Predicted)
• Density: 1.205±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzene, 1,4-dimethoxy-2-(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,4-dimethoxy-2-(trifluoromethyl)-(84355-10-2)
• EPA Substance Registry System: Benzene, 1,4-dimethoxy-2-(trifluoromethyl)-(84355-10-2)

Safety Data

• Hazardous Substances Data: 84355-10-2(Hazardous Substances Data)

Upstream product

• 421-83-0 trifluoromethane sulfonyl chloride 
• 150-78-7 1,4-dimethoxybezene 
• 80783-62-6 N-Trifluoromethyl-N-nitrosobenzenesulfonamide 
• 99964-09-7 N-trifluoromethyl-N-nitrosotrifluoromethanesulfon-amide 
• 41804-89-1 potassium triflinate 
• 107099-99-0 2,5-dimethoxyphenylboronic acid 
• 129946-88-9 Umemoto's reagent 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2926-29-6 Langlois reagent 
• 407-25-0 trifluoroacetic anhydride 
• 75-63-8 Bromotrifluoromethane 
• 2314-97-8 iodotrifluoromethane 
• 1415694-01-7 N-(4-cyanophenyl)-1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide 
• 2926-30-9 sodium triflate 

Relevant articles and documents

Recyclable alkylated Ru(bpy)32+ complex as a visible-light photoredox catalyst for perfluoroalkylation

A recyclable Ruthenium tris [4,4′-bis (dinonylmethyl)-2,2′-bipyridine] (Ru[(DNM)2bpy]32+) photocatalyst (PC) was synthesized. Hexane-phase-selective solubility allowed its simple and efficient separation from reaction products via solvent extraction. The excellent catalytic activity and recoverability were demonstrated in batch and flow perfluoroalkylation reactions of coumarin under visible-light irradiation. High reaction rates and easy reusability of the catalyst make this approach attractive for large-scale applications.

Exploring the Structure and Performance of Cd–Chalcogenide Photocatalysts in Selective Trifluoromethylation

The field of heterogeneous photoredox catalysis has grown substantially and impacted organic synthesis because of the affordability and reusability of catalysts. This study reports radical trifluoromethylation with Cd–chalcogenide semiconductors. Cd semiconductors, particularly CdSe, are readily available, commercial, visible-light-responsive, heterogeneous photocatalysts. The potential of readily available Cd semiconductors, particularly CdSe, is confirmed by their increased photocatalytic activity toward trifluoromethylation with various substrates, such as (hetero)arenes and vinylic amides/acids, via addition, cyclization, and decarboxylation under visible light. The economic significance of this strategy is also highlighted through the scalable synthesis of biologically active molecules followed by catalyst reuse. Moreover, these catalysts are relatively inexpensive compared with transition metal-based homogeneous photocatalysts, presently used in organic synthesis.

5-HT2A AGONISTS FOR USE IN TREATMENT OF DEPRESSION

The present invention relates to agonists of the 5-HT2A serotonin receptors and their medical uses. In one aspect the invention relates to 5-HT2A agonists of formula (I). In second aspect, the invention relates to selective 5-HT2A agonists of formula (II). In another aspect, the invention relates to mixed 5-HT2A/5-HT2C agonists of formula (III). In yet another aspect, the invention relates to 5-HT2A agonists for use in the treatment of a depressive disorder, more particular a 5-HT2A agonist for the use in the treatment of treatment-resistant depression.

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.

Regioselective C-H Trifluoromethylation of Aromatic Compounds by Inclusion in Cyclodextrins

A regioselective radical C-H trifluoromethylation of aromatic compounds was developed using cyclodextrins (CDs) as additives. The C-H trifluoromethylation proceeded with high regioselectivity to afford the product in good yield, even on the gram scale. In the presence of CDs, some substrates underwent a single trifluoromethylation selectively, whereas mixtures of single- and double-trifluoromethylated products were formed in the absence of the CD. 1H NMR experiments indicated that the regioselectivity was controlled by the inclusion of a substrate inside the CD cavity.

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

Solid-State Radical C?H Trifluoromethylation Reactions Using Ball Milling and Piezoelectric Materials

The application of piezoelectricity for the generation of trifluoromethyl (CF3) radicals is reported together with the development of a method for the mechanochemical C?H trifluoromethylation of aromatic compounds. As compared to conventional solution-based approaches, this mechanoredox C?H trifluoromethylation enables cleaner and more sustainable access to a wide range of trifluoromethylated N-heterocycles and peptides, which are important structural motifs in modern drug discovery. This study thus represents an important milestone for future applications of mechanoredox systems to medicinal and pharmaceutical science.

Electrophotocatalytic Undirected C?H Trifluoromethylations of (Het)Arenes

Electrophotochemistry has enabled arene C?H trifluoromethylation with the Langlois reagent CF3SO2Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant-free approach for the generation of the CF3 radical. The electrophotochemistry was carried out in an operationally simple manner, setting the stage for challenging C?H trifluoromethylations of unactivated arenes and heteroarenes. The robust nature of the electrophotochemical manifold was reflected by a wide scope, including electron-rich and electron-deficient benzenes, as well as naturally occurring heteroarenes. Electrophotochemical C?H trifluoromethylation was further achieved in flow with a modular electro-flow-cell equipped with an in-operando monitoring unit for on-line flow-NMR spectroscopy, providing support for the single electron transfer processes.

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.

CATALYST-FREE AND REDOX-NEUTRAL INNATE TRIFLUOROMETHYLATION AND ALKYLATION OF (HETERO)AROMATICS ENABLED BY LIGHT

The present disclosure relates to reagents and method for performing trifluoromethylation, difluoromethylation or alkylation of aromatic or heteroaromatic rings in a redox-neutral manner without any catalyst which are enabled by light. In addition, there are methods for synthesizing the starting reagents used in the trifluoromethylation, difluoromethylation or alkylation reactions.