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
• Article Data: 9

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 
• 129946-88-9 Umemoto's reagent 
• 152376-94-8 ⁿBu₄N⁺[Cu(CF₃)₄]^- 

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.

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.

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.