19161-30-9

Upstream product

• 773-82-0 Pentafluorobenzonitrile 
• 127-09-3 sodium acetate 
• 532-32-1 sodium benzoate 
• 27318-28-1 2,3,4,5,6-pentafluorobenzaldehyde oxime 
• 344-04-7 bromopentafluorobenzene 
• 20925-85-3 pentachlorobenzonitrile 
• 653-37-2 perfluorobenzaldehyde 
• 344-07-0 1-chloro-2,3,4,5,6-pentafluorobenzene 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 

Downstream Products

• 70627-93-9 4-Octyl-benzoic acid 4-cyano-2,3,5,6-tetrafluoro-phenyl ester 
• 70627-94-0 4-Heptyloxy-benzoic acid 4-cyano-2,3,5,6-tetrafluoro-phenyl ester 
• 217825-63-3 4-cyano-2,3,5,6-tetrafluorophenyl acrylate 
• 652-34-6 2,3,5,6-tetrafluoro-4-hydroxybenzoic acid 
• 1228871-03-1 (p-cyano-(tetrafluoro)-phenoxy)trimethylsilane 

Relevant academic research and scientific papers

Mechanism of Oxidative Activation of Fluorinated Aromatic Compounds by N-Bridged Diiron-Phthalocyanine: What Determines the Reactivity?

The biodegradation of compounds with C?F bonds is challenging due to the fact that these bonds are stronger than the C?H bond in methane. In this work, results on the unprecedented reactivity of a biomimetic model complex that contains an N-bridged diiron-phthalocyanine are presented; this model complex is shown to react with perfluorinated arenes under addition of H2O2 effectively. To get mechanistic insight into this unusual reactivity, detailed density functional theory calculations on the mechanism of C6F6 activation by an iron(IV)-oxo active species of the N-bridged diiron phthalocyanine system were performed. Our studies show that the reaction proceeds through a rate-determining electrophilic C?O addition reaction followed by a 1,2-fluoride shift to give the ketone product, which can further rearrange to the phenol. A thermochemical analysis shows that the weakest C?F bond is the aliphatic C?F bond in the ketone intermediate. The oxidative defluorination of perfluoroaromatics is demonstrated to proceed through a completely different mechanism compared to that of aromatic C?H hydroxylation by iron(IV)-oxo intermediates such as cytochrome P450 Compound I.

Catalytic defluorination of perfluorinated aromatics under oxidative conditions using N-bridged diiron phthalocyanine

Carbon-fluorine bonds are the strongest single bonds in organic chemistry, making activation and cleavage usually associated with organometallic and reductive approaches particularly difficult. We describe here an efficient defluorination of poly- and perfluorinated aromatics under oxidative conditions catalyzed by the μ-nitrido diiron phthalocyanine complex [(Pc)Fe III(μ-N)FeIV(Pc)] under mild conditions (hydrogen peroxide as the oxidant, near-ambient temperatures). The reaction proceeds via the formation of a high-valent diiron phthalocyanine radical cation complex with fluoride axial ligands, [(Pc)(F)FeIV(μ-N)FeIV(F) (Pc+?)], which was isolated and characterized by UV-vis, EPR, 19F NMR, Fe K-edge EXAFS, XANES, and Kβ X-ray emission spectroscopy, ESI-MS, and electrochemical techniques. A wide range of per- and polyfluorinated aromatics (21 examples), including C6F6, C6F5CF3, C6F5CN, and C6F5NO2, were defluorinated with high conversions and high turnover numbers. [(Pc)FeIII(μ-N)Fe IV(Pc)] immobilized on a carbon support showed increased catalytic activity in heterogeneous defluorination in water, providing up to 4825 C-F cleavages per catalyst molecule. The μ-nitrido diiron structure is essential for the oxidative defluorination. Intramolecular competitive reactions using C6F3Cl3 and C6F3H 3 probes indicated preferential transformation of C-F bonds with respect to C-Cl and C-H bonds. On the basis of the available data, mechanistic issues of this unusual reactivity are discussed and a tentative mechanism of defluorination under oxidative conditions is proposed.

REACTION OF POLYFLUORINATED AROMATIC COMPOUNDS WITH SODIUM NITRITE

The reactions of polyfluorinated aromatic compounds with sodium nitrite lead to the formation of products from N- and O-substitution of the fluorine atoms in the aromatic ring.The increase in the nucleophilic mobility of the fluorine atoms with the introduction of electron-withdrawing substituents into the ring promotes the formation of the O-substitution products.

2,3,5,6-Tetrafluorophenyl (meth) acrylates and method for production thereof

2,3,5,6-Tetrafluorophenyl (meth)acrylates represented by the general formula I: STR1 wherein R is H or CH3 and X is H or CN are disclosed. These compounds are obtained by the reaction of 4-cyano-substituted or unsubstituted 2,3,5,6-tetrafluorop