776-16-9

Upstream product

• 880-78-4 pentafluoronitrobenzen 
• 69173-92-8 4-azido-1-nitro-2,3,5,6-tetrafluorobenzene 
• 530102-89-7 1-(4-nitro-2,3,5,6-tetrafluorophenyl)-4-trimethylsilyl-2,4-diaza-1,3-dithia-2,3-butadiene 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 530102-84-2 2,3,5,6-tetrafluoro-4-nitrophenylsulfenyl chloride 
• 107954-62-1 2,3,5,6-tetrafluoro-4-nitrobenzenethiol 

Downstream Products

• 14851-19-5 2-Methoxy-4-amino-3,5,6-trifluor-nitrobenzol 
• 1423543-38-7 C₆F₆N₂O₂ 
• 1887-77-0 4-NO₂-C₆F₄N(CH₃)2 
• 743-81-7 N,N'-bis(trifluoroacetyl)-2,3,5,6-tetrafluoro-1,4-phenylenediamine 
• 74632-45-4 4,4'-dinitrooctafluoroazobenzene 
• 69642-07-5 C₆HCl₂F₄N 
• 14851-15-1 2-Methylamino-4-amino-3,5,6-trifluornitrobenzol 
• 14851-17-3 2-Dimethylamino-4-amino-3,5,6-trifluornitrobenzol 
• 830-51-3 2,4-Difluor-6-nitro-1,3,5-triamino-benzol 
• 17823-37-9 1-bromo-2,3,5,6-tetrafluoro-4-nitrobenzene 
• 1198-64-7 2,3,5,6-tetrafluorobenzene-1,4-diamine 
• 74632-39-6 4-nitro-2,3,5,6-tetrafluoro-N,N-dichloroaniline 
• 2106-00-5 2,4,5-trifluoro-6-nitro-1,3-phenylenediamine 

Relevant academic research and scientific papers

Synthesis and Optimization of Kv7 (KCNQ) Potassium Channel Agonists: The Role of Fluorines in Potency and Selectivity

Based on the potent Kv7 agonist RL-81, we prepared new lead structures with greatly improved selectivity for Kv7.2/Kv7.3 over related potassium channels, i.e., Kv7.3/Kv7.5, Kv7.4, and Kv7.4/7.5. RL-36 and RL-12 maintain an agonist EC2x of ca. 1 μM on Kv7.2/Kv7.3 in a high-throughput assay on an automated electrophysiology platform in HEK293 cells but lack activity on Kv7.3/Kv7.5, Kv7.4, and Kv7.4/7.5, resulting in a selectivity index SI > 10. RL-56 is remarkably potent, EC2x 0.11 ± 0.02 μM, and still shows an SI = 2.5. We also identified analogues with significant selectivity for Kv7.4/Kv7.5 over Kv7.2/Kv7.3. The extensive use of fluorine in iterative core structure modifications highlights the versatility of these substituents, including F, CF3, and SF5, to span orders of magnitude of potency and selectivity in medicinal chemistry lead optimizations.

SELECTIVE POTASSIUM CHANNEL AGONISTS

Selective potassium channel agonists and methods of use thereof are disclosed. A compound, or a pharmaceutically acceptable salt thereof, having a formula (I) wherein R1 is H or optionally-substituted alkyl; R2 is optionally-substituted C1-C6 alkyl or optionally- substituted cyclopropyl; R3 and R4 are each independently H or optionally- substituted alkyl; R5 is H, optionally-substituted alkyl, acyl, or alkoxycarbonyl; R6 and R7 are each independently H, optionally- substituted alkyl, or R6 and R7 together form a carbocycle; R8 is substituted phenyl or optionally-substituted pyridinyl, provided that if R8 is substituted phenyl, then R2 is optionally-substituted cyclopropyl; and R9, R10 and R11 are each independently H, halo, or optionally- substituted alkyl.

Continuous flow synthesis of difluoroamine systems by direct fluorination

Continuous flow methodology for the synthesis of perfluoroaryl difluoroamine derivatives by reaction of fluorine gas with an appropriate perfluoroaniline substrate is described, further demonstrating the efficient use of flow regimes for reactions involvi

CHARGE-TRANSPORT MATERIALS, METHODS OF FABRICATION THEREOF, AND METHODS OF USE THEREOF

Briefly described, embodiments of this disclosure include charge-transport materials, methods of forming charge-transport materials, and methods of using the charge-transport materials.

Fluorinated 1,3λ4δ2,2,4-benzodithiadiazines - A synthetic, structural and theoretical study

The series of title compounds has been prepared through both electrophilic (C6HnF5-n-N=S=N-SiMe3 + SCl2) and nucleophilic (C6HF4_S-N=S=N-SiMe3 + CsF) intramolecular ortho-cyclisation reactions, and the former route seems to be the more effective. High regioselectivity of the ring-closing procedures is observed in both cases. The compounds were characterised by X-ray crystallography and multinuclear (1H, 13C, 15N and 19F) NMR spectroscopy. In accordance with GIAO calculations, 15N{1H} experiments and the effects observed on complete substitution of hydrogen by fluorine, the high-field signal in the 15N NMR spectra can be assigned to N-4 and the low-field signal to N-2. In the crystal, 5,6,7-trifluoro-(5) and 5,6,8-trifluoro-1,3λ4δ22,4- benzodithiadiazine (6) are planar, whereas the 6,8-difluoro derivative 3 is bent along the S1...N4 line by 8.3°. According to NICS calculations the heterocycle moiety in this compound class is antiaromatic while the carbocycle is aromatic. The fluorine substituents increase the aromaticity - and in some cases (especially when a fluorine atom is present in the 8-position) the antiaromaticity - of the corresponding rings. The ortho-fluoro-containing starting material C6HnF5-n-N=S=N-SiMe3 (n = 2: 10) cyclises to the fluorinated 2,1,3-benzothiadiazole 27 upon treatment with CsF instead of SCl2. For starting compound 6-HC6F4-S-N=S=N-SiMe3 (14) the planar (Z,E) configuration features a short intramolecular H...N contact, as evidenced by X-ray diffraction. Both the reaction pathways mentioned are also discussed. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2003.

Polyhalogenonitrobenzenes and derived compounds: Part 5. Improved preparations of 1,2,3,4-tetrafluoro-5,6-dinitrobenzene and 3,4,5,6-tetrafluoro-1,2-phenylenediamine, and the use of the latter for the synthesis of tetrafluorobenzheterocycles

The preparation of 2,3,4,5-tetrafluoro-6-nitroaniline (3) by amination of pentafluoronitrobenzene has been speeded up, scaled up and the yield increased by controlling the reaction by TLC monitoring and using 'dry column' chromatography. Compound (3) was readily converted to 1,2,3,4-tetrafluoro-5,6-dinitrobenzene (2) by peroxytrifluoroacetic acid and to 3,4,5,6-tetrafluoro-1,2-phenylenediamine (1) by SnCl2/HCl, Compound (1) was shown to be a versatile intermediate for the synthesis of tetrafluoro-benzimidazoles, -triazoles and -quinoxalines. The fungicidal activity of the latter are reported here.

Reactions of polyfluoroarenes with hexamethyldisilazane and with 1,1,1-trimethyl-N,N-bis(trimethylsilyl)stannaneamine in the presence of caesium fluoride

Hexamethyldisilazane and 1,1,1-trimethyl-N,N-bis(trimethylsilyl)stannaneamine aminate pentafluoropyridine, octafluorotoluene, pentafluorobenzonitrile, pentafluoronitrobenzene and pentafluorobenzene sulphonyl fluoride in the presence of caesium fluoride with formation of the corresponding perfluorinated aryl amines (ArNH2), diarylamines (Ar2NH) and triarylamines (Ar3N) (where the amine functions are in positions 4 relative to the arene substituent). - Keywords: Polyfluoroarenes; Hexamethyldisilazane; Caesium fluoride; Silylated amines

Rapid and selective reduction of functionalized fluoroaryl azides to the corresponding anilines with stannous chloride dihydrate

Nitrofluorophenyl azide 1, azidofluorobenzaldehyde 2, azidofluorobenzoate ester 3, and aminotrifluorophenyl azide 4 were selectively reduced in high yield to the corresponding anilines 5-8 with excess stannous chloride dihydrate in 2:1 ethyl acetate/ethan

REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. X. AMINATION OF POLYFLUORINATED AROMATIC COMPOUNDS CONTAINING ELECTRON-WITHDRAWING SUBSTITUENTS

It was shown for the case of 2,4-difluoro-, 2,4,6-trifluoro-, and pentafluoronitrobenzenes that both liquid ammonia and sodium amide in liquid ammonia are effective reagents for aminodefluorination with respect to the fluorine derivatives of nitrobenzene.The observed tendency for the ortho-orientation with respect to the nitro group to change to para-orientation with increase in the number of fluorine atoms is more clearly defined for sodium amide than for liquid ammonia as nucleophile on account, clearly, of the stabilization of the transition state of ortho-substitution in the latter case by an intramolcular hydrogen bond.