21894-26-8

Basic information

• Product Name: C₁₂H₁₅F₃NO
• Synonyms: C₁₂H₁₅F₃NO
• CAS NO: 21894-26-8
• Molecular Weight: 246.252
• Mol File: 21894-26-8.mol

Chemical Properties

• CAS DataBase Reference: C₁₂H₁₅F₃NO(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₂H₁₅F₃NO(21894-26-8)
• EPA Substance Registry System: C₁₂H₁₅F₃NO(21894-26-8)

Safety Data

• Hazardous Substances Data: 21894-26-8(Hazardous Substances Data)

Upstream product

• 2314-97-8 iodotrifluoromethane 
• 3376-24-7 (Z)-N-benzylidene-2-methylpropan-2-amine oxide 
• 95776-86-6 1,1,2,2-Tetrakis(trifluormethylthio)-1,2-bis(pentafluorphenylthio)ethan 
• 81464-62-2 1,1,2,2-Tetrakis(trifluormethylthio)-1,2-bis-(trifluormethylseleno)ethan 
• 81464-63-3 1,1,2,2-Tetrakis(trifluormethylseleno)-1,2-bis-(trifluormethylthio)ethan 
• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 887144-94-7 Togni's reagent II 
• 30765-95-8 N-p-toluenesulfonyl-2-vinylaniline 
• 95-50-1 1,2-dichloro-benzene 
• 152376-94-8 ⁿBu₄N⁺[Cu(CF₃)₄]^- 
• 129946-88-9 Umemoto's reagent 

Relevant articles and documents

M?C Bond Homolysis in Coinage-Metal [M(CF3)4]? Derivatives

A comparative study of the homoleptic [M(CF3)4]? complexes of all three coinage metals (M=Cu, Ag, Au) reveals that homolytic M?C bond cleavage is favoured in every case upon excitation in the gas phase (CID-MS2). Homolysis also occurs in solution by photochemical excitation. Transfer of the photogenerated CF3. radicals to both aryl and alkyl carbon atoms was also confirmed. The observed behaviour was rationalized by considering the electronic structure of the involved species, which all show ligand-field inversion. Moreover, the homolytic pathway constitutes experimental evidence for the marked covalent character of the M?C bond. The relative stability of these M?C bonds was evaluated by energy-resolved mass spectrometry (ERMS) and follows the order CuAg?Au. The qualitatively similar and rather uniform behaviour experimentally observed for all three coinage metals gives no ground to suggest variation in the metal oxidation state along the group.

Visible-Light-Driven Aza-ortho-quinone Methide Generation for the Synthesis of Indoles in a Multicomponent Reaction

A visible-light-driven radical-mediated strategy for the in situ generation of aza-ortho-quinone methides from 2-vinyl-substituted anilines and alkyl radical precursors is described. This process enables an efficient multicomponent reaction of 2-vinylanilines, halides, and sulfur ylides, and has a wide substrate scope and good functional group tolerance. Treatment of the cycloaddition products with a base leads to densely functionalized indoles in a single-flask operation.

C?H Bond Trifluoromethylation of Arenes Enabled by a Robust, High-Valent Nickel(IV) Complex

The robust, high-valent NiIV complex [(Py)2NiIVF2(CF3)2] (Py=pyridine) was synthesized and fully characterized by NMR spectroscopy, X-ray diffraction, and elemental analysis. It reacts with aromatic compounds at 25 °C to form the corresponding benzotrifluorides in nearly quantitative yield. The monomeric and dimeric NiIIICF3 complexes 2?Py and 2 were identified as key intermediates, and their structures were unambiguously determined by EPR spectroscopy and X-ray diffraction. Preliminary kinetic studies in combination with the isolation of reaction intermediates confirmed that the C?H bond-breaking/C?CF3 bond-forming sequence can occur both at NiIVCF3 and NiIIICF3 centers.

An External-Catalyst-Free Trifluoromethylation/Cyclization Strategy to Access Trifluoromethylated-Dihydroisoquinolinones/Indolines with Togni Reagent II

A novel and efficient CF3 radical-involved external-catalyst-free trifluoromethylation/cyclization methodology to access a group of new trifluoromethylated dihydroisoquinolinones was developed, by reacting different N-allylbenzamides with Togni

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.

N-9 Alkylation of purines via light-promoted and metal-free radical relay

A metal-free and light-promoted approach to the synthesis of N-9 alkylated purine nucleoside derivatives, via a CF3 radical triggered radical relay pathway, has been developed. Purine nucleoside derivatives were prepared regioselectively in good to high yields. Photosensitizers and metals are free in this transformation. Visible light or even sunlight can be used as the source of light for the reactions.

CuCl-catalyzed ortho trifluoromethylation of arenes and heteroarenes with a pivalamido directing group

The CuCl catalyzed direct trifluoromethylation of sp2 C-H bonds has been realized, using the Togni reagent as the CF3 source. This reaction achieves the goal of regio-selectively converting C-H into C-CF 3 with ecological and readily available starting materials.

Oxidative cleavage of CH3 and CF3 radicals from BOXAM nickel complexes

Oxidation of the nickel complexes [(BOXAM)Ni(R)] (HBOXAM = bis((4-isopropyl-4,5-dihydrooxazol-2-yl)phenyl)amine) with R = CF3, CH3, Cl leads to the corresponding radical cationic complexes, which rapidly undergo homolytic Ni-R bond s

DARSTELLUNG UND THERMOLYSE VON HEXAKIS(PERFLUORORGANYLTHIO/SELENO)ETHANEN

Thiocarbonylcompounds such as 1a, 1b, 1c, 1d, 1e and 1f were prepared and irradiated with UV-light in hexane solution.The products obtained in this photolyses are 3a, 3b and 3c.Only 3c dissociates in the temperature range 140-190 deg C reversible to 2c.The others, 3a and 3b, decompose yielding bis(trifluoromethyl)diselenide, 6b and 6d, without forming the corresponding methyl radical 2a and 2b.This was proved by spin-trapping experiments utilizing phenyl-t-butylnitrone.Attempts to prepare 3e were unsuccessful but led to the new compounds 7a, 7b, 7c, 1,1,1-tris(trifluoromethylseleno)ethan (7d) and, surprisingly, 9.Physical and spectroscopic data of the newly prepared substances are provided.