3382-78-3

Upstream product

• 371-40-4 4-fluoroaniline 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 109773-02-6 2-(4-Fluoro-phenyl)-2H-indazole-3-carbonitrile 
• 109773-05-9 (4-Fluoro-phenyl)-(3-methoxy-1-oxy-cinnolin-4-yl)-amine 
• 109772-90-9 (4-Fluoro-phenylamino)-(2-nitro-phenyl)-acetonitrile 
• 81265-90-9 2-(4-fluorophenyl)–2H-indazole 
• 1204524-88-8 C₂₈H₂₀F₂N₄O₂ 
• 109772-97-6 2-(4-Fluoro-phenyl)-1-oxy-2H-indazole-3-carbonitrile 

Relevant academic research and scientific papers

New yellow-emitting iridium(III) complexes containing 2-phenyl-2H-indazole-based ligands for high efficient OLEDs with EQE over 25%

Six new pidz-based bis-cyclometalated Ir(III) complexes (Ir1-Ir6) have been synthesized and characterized. These complexes contain 2-phenyl-2H-indazole (pidz, 2a), 2-(4-fluorophenyl)–2H-indazole (fpidz, 2b), 2-(p-tolyl)–2H-indazole (ch3pidz, 2c), 2-(4-(trifluoromethyl)phenyl)–2H-indazole (cf3pidz, 2d), 2-(2,4-difluorophenyl)–2H-indazole (2,4-f2pidz, 2e) and 2-(3,5-difluorophenyl)–2H-indazole (3,5-f2pidz, 2f) as cyclometalated (C∧N) ligands, and acetylacetone (acacH) as ancillary ligand. The crystal structure of Ir2 has been determined by X-ray analysis. Different substituents of C∧N ligand in Ir2-Ir6 induce either a bathochromic or hypsochromic shift in the absorption spectra relative to the parent complex Ir1. The phenomenon is further well explained by DFT calculation and electrochemical study. All of the iridium(III) complexes are yellow emissive with quantum yields of 13.1–32.3% and lifetimes of 1.32–1.77 μs in solution at room temperature. We demonstrate that their emission originates from a hybrid 3MLCT/3ILCT/3LLCT excited state on the basis of the experimental and theoretical investigation. The corresponding yellow-emitting devices based on complexes Ir1, Ir2 and Ir4 can produce efficient electrophosphorescence with a luminance efficiency of 35.1–52.2 cd·A-1, a power efficiency of 20.8–32.1 lm·W?1 and an external quantum efficiency of up to 25.6%. All these EL data definitely suggest the bulky –CF3 skeleton in the doped materials could benefit the fabrication of high-efficiency phosphorescent OLEDs.

Synthesis, antiprotozoal activity, and cheminformatic analysis of 2-phenyl-2h-indazole derivatives

Indazole is an important scaffold in medicinal chemistry. At present, the progress on synthetic methodologies has allowed the preparation of several new indazole derivatives with interesting pharmacological properties. Particularly, the antiprotozoal activity of indazole derivatives have been recently reported. Herein, a series of 22 indazole derivatives was synthesized and studied as antiprotozoals. The 2-phenyl-2H-indazole scaffold was accessed by a one-pot procedure, which includes a combination of ultrasound synthesis under neat conditions as well as Cadogan’s cyclization. Moreover, some compounds were derivatized to have an appropriate set to provide structure-activity relationships (SAR) information. Whereas the antiprotozoal activity of six of these compounds against E. histolytica, G. intestinalis, and T. vaginalis had been previously reported, the activity of the additional 16 compounds was evaluated against these same protozoa. The biological assays revealed structural features that favor the antiprotozoal activity against the three protozoans tested, e.g., electron withdrawing groups at the 2-phenyl ring. It is important to mention that the indazole derivatives possess strong antiprotozoal activity and are also characterized by a continuous SAR.

Tunable Emission Color of Iridium(III) Complexes with Phenylpyrazole Derivatives as the Main Ligands for Organic Light-Emitting Diodes

Seven cyclometalated iridium(III) complexes Ir1-Ir7 based on phenylpyrazole derivatives as main ligands and tetraphenylimidodiphosphinate (tpip) as the ancillary ligand were synthesized and fully characterized. The proligands of 1-[4-(trifluoromethyl)phenyl]-1H-pyrazole (cf3ppz, 2a), substituted phenyl-2H-indazole {2-phenyl-2H-indazole (h-1-pidz, 2b), 2-(4-fluorophenyl)-2H-indazole (f-1-pidz, 2c), and 2-[4-(trifluoromethyl)phenyl]-2H-indazole (cf3-1-pidz, 2d)}, and substituted phenyl-1H-indazole {1-phenyl-1H-indazole (h-7-pidz, 2e), 1-(4-fluorophenyl)-1H-indazole (f-7-pidz, 2f), and 1-[4-(trifluoromethyl)phenyl]-1H-indazole (cf3-7-pidz, 2g)} were prepared with good yields. The emission maxima of all Ir(III) complexes can be tuned from 453 to 576 nm with different photoluminescence quantum yields (10.4-70.9%) by varying the type of substituent on the different main ligand frameworks. The organic light-emitting diodes using Ir(III) complexes as the emitters with blue, bluish-green, and yellow colors exhibit a maximum current efficiency and an external quantum efficiency of 39.2 cd A-1 and 14.8%, respectively.

A Facile One-Step Synthesis of 2-Arylindazoles via Reductive Cyclization of N-(2-nitroarylidene)amines

A mild and efficient synthesis of 2-arylindazole derivatives via the reductive cyclization of nitro-aryl substrates mediated by a low-valent titanium reagent (TiCl4/Sm/Et3N) has been developed. The attractive features of the current method include an N-N bond formation and the selective reduction of the =C-N bond and nitro group, both of which were easily achieved in one-pot by controlling the pH of the reaction mixture.

Oriented synthesis and in vitro anticancer activity of biquinazoline-2,2'- diones

The synthesis of a series of biquinazoline-2,2'-diones starting from o-nitrobenzaldehydes, anilines, and triphosgene is presented. This general approach features a novel and easy way for access to the target products. The mechanistic course of the reaction suggests the involvement of reduction, coupling, and cyclization by one-pot. These compounds were also investigated in vitro for anticancer activity, and some were found to have good anticancer activity.

o-Nitrobenzylidene Compounds. Part 3. Formation of 4-Arylamino-3-methoxycinnoline 1-Oxides from N-o-Nitrobenzylideneanilines, Cyanide Ion, and Methanol: the Intermediacy of 2-Aryl-3-cyano-2H-indazole 1-Oxides

The N-o-nitrobenzylidene derivatives of variously substituted anilines (7) have been cyclised by potassium cyanide in methanol, to give 4-arylamino-3-methoxycinnoline 1-oxides (9), the structures of which have been confirmed by independent synthesis of one representative .These cinnoline oxides are the main products (sometimes the only isolated products) when the amine-derived ring in (7) is ortho-substituted; in other cases the cinnoline oxides are minor products formed along with 2-aryl-3-cyano-2H-indazoles (10).In the latter group of reactions, the primary cyclisation products are 2-aryl-3-cyano-2H-indazole 1-oxides (8): these have then either been reduced to the indazoles in the basic methanolic medium, or have undergone ring-opening and recyclisation to give the cinnoline oxides (9).In the other group, where indazole oxides (8) cannot usually be isolated, their intermediacy in cinnoline oxide formation remains a possibility, although other mechanistic pathways can be envisaged.Some 'borderline' cases are identified and discussed.