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Usage

Uses

Used in Pharmaceutical Research and Development:
1-(2,6-Dichlorophenyl)hydrazine is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block in the creation of new drugs with potential therapeutic benefits.
Used in Agrochemical Research and Development:
Similarly, in the agrochemical industry, 1-(2,6-Dichlorophenyl)hydrazine serves as a key intermediate in the synthesis of agrochemicals aimed at enhancing crop protection and yield.
Used in Organic Synthesis:
1-(2,6-Dichlorophenyl)hydrazine is utilized as a precursor in organic synthesis, playing a crucial role in the preparation of a wide range of organic compounds for various applications across different industries.
Used in Antitumor and Antituberculosis Drug Development:
1-(2,6-Dichlorophenyl)hydrazine has been studied for its potential antitumor and antituberculosis activities, indicating its use as a lead compound in the development of new therapeutic agents against cancer and tuberculosis.
Safety Considerations:
Due to the potentially hazardous nature of 1-(2,6-Dichlorophenyl)hydrazine, it is essential to exercise proper safety precautions during its handling, storage, and use to minimize risks to human health and the environment.

InChI:InChI=1/C6H6Cl2N2/c7-4-2-1-3-5(8)6(4)10-9/h1-3,10H,9H2

Upstream product

• 50709-36-9 (2,6-dichlorophenyl)hydrazine monohydrochloride 
• 608-31-1 2,6-Dichloroaniline 
• 43142-73-0 2,6-Dichloro-benzenediazonium; chloride 

Downstream Products

• 89270-45-1 5-Methyl-2H-pyrazole-3-carboxylic acid N'-(2,6-dichloro-phenyl)-hydrazide 
• 76210-62-3 1-[N'-(2,6-Dichloro-phenyl)-hydrazino]-3-phenoxy-propan-2-ol; hydrochloride 
• 89270-65-5 C₁₂H₁₀Cl₂N₄O₂ 
• 94447-38-8 1-Acetyl-5-methyl-1H-pyrazole-3-carboxylic acid N'-(2,6-dichloro-phenyl)-hydrazide 
• 94447-39-9 C₁₄H₁₂Cl₂N₄O₃ 
• 65106-10-7 thiazolidin-2-one (2,6-dichloro-phenyl)-hydrazone 
• 74478-58-3 phthalaldehydic acid phenylhydrazone 
• 588-64-7 (E)-1-benzylidene-2-phenylhydrazine 

Relevant academic research and scientific papers

Proton transfer reactions of N-aryl triazolium salts: Unusual ortho-substituent effects

Previous studies of the C(3)-hydrogen/deuterium exchange reactions of the triazolium ion conjugate acids of triazolyl N-heterocyclic carbenes revealed a change of mechanism under acidic conditions with N1-protonation to a dicationic salt. Interestingly, the data suggested an increase in pKaN1 in the presence of a N-pentafluorophenyl substituent relative to other N-aryl substituents with hydrogens or methyl substituents rather than fluorines at the ortho-positions. To probe the presence of an apparent donor effect of a N-pentafluorophenyl substituent, which differs from the more common electron withdrawing effect of this group, we have studied the analogous deuterium exchange reactions of four triazolium salts with heteroatoms or heteroatom substituents in the 2-position and/or 6-position of the N-aryl ring. These include triazolium salts with N-2,4,6-tribromophenyl 11, N-2,6-dichlorophenyl 12, N-2-pyridyl 13 and N-2-pyrimidinyl 14 substituents. The log kex - pD profiles for 11, 12 and 14 were found to show similar trends at lower pDs as for the previously studied N-pentafluorophenyl triazolium salt, hence supporting the presence an apparent donor effect on pKaN1. Surprisingly, the log kex - pD profile for N-pyridyl salt 13 uniquely showed acid catalysis at lower pDs. We propose herein that this data is best explained by invoking an intramolecular general base role for the N-(2-pyridyl) substituent in conjunction with N1-protonation on the triazolium ring. Finally, the second order rate constants for deuteroxide ion catalysed C(3)-H/D exchange (kDO, M-1 s-1), which could be obtained from data at pDs 1.5, were used to provide estimates of C(3)-carbon acid pKaC3 values for the four triazolium salts 11-14.

Towards the Molecular Design of Spin-Crossover Complexes of 2,6-Bis(pyrazol-3-yl)pyridines

The molecular design of spin-crossover complexes relies on controlling the spin state of a transition metal ion by proper chemical modifications of the ligands. Herein, the first N,N’-disubstituted 2,6-bis(pyrazol-3-yl)pyridines (3-bpp) are reported that, against the common wisdom, induce a spin-crossover in otherwise high-spin iron(II) complexes by increasing the steric demand of a bulky substituent, an ortho-functionalized phenyl group. As N,N’-disubstituted 3-bpp complexes have no pendant NH groups that make their spin state extremely sensitive to the environment, the proposed ligand design, which may be applicable to isomeric 1-bpp or other families of popular bi-, tri- and higher denticity ligands, opens the way for their molecular design as spin-crossover compounds for future breakthrough applications.

Anthranilic diamides derivatives as potential ryanodine receptor modulators: Synthesis, biological evaluation and structure activity relationship

A series of novel anthranilic diamides derivatives (7a–s) containing halogen, trifluoromethyl group and cyano group were designed, synthesized, and characterized by melting point, 1H NMR, 13C NMR and elemental analyses. The bioactivity revealed that most of them showed moderate to excellent activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). Above all, the larvicidal activity of 7o against oriental armyworm was 100% and 40% at 0.25 and 0.1 mg L?1, comparable to that of the standard chlorantraniliprole (100%, 0.25 mg L?1 and 20%, 0.1 mg L?1). What is more, 7o against diamondback moth displayed 90% insecticidal activity at 0.01 mg L?1, superior to chlorantraniliprole (45%, 0.01 mg L?1). The experiments 7o on the American cockroach (Periplaneta Americana) heart beating rates (Dorsal vessel) and contractile force were compared with chlorantraniliprole. In addition, 7o could affect the calcium homeostasis in the central neurons of the third larvae of oriental armyworm, which revealed that the ryanodine receptor is the potential target of 7o. The density functional theory (DFT) calculation results revealed the amide bridge, the benzene ring of anthraniloyl moiety and pyrazole ring might play an important role in the insecticidal activity through hydrophobic interactions and π-π conjugations.

Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi

A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.

Pyrazolones as inhibitors of 11B-hydroxysteroid dehydrogenase

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, type II diabetes mellitus and metabolic syndrome.

Antiimplantation Agents: Part I - 1-Arylthiosemicarbazides

Several 1-arylthiosemicarbazides, 2-arylhydrazinothiazolines and 2-arylhydrazinodihydrothiazines have been examined for their antiimplantation activity in rats.Among the active compounds, 4-methyl-1-(3,5-bistrifluoromethylphenyl)thiosemicarbazide (3, C 2696-Go) and the corresponding 4,4-dimethyl (47), ethyl (4), n-butyl (5) and allyl (6) derivatives completely inhibit implantation at doses 10, 3, 20, 20 and 30 mg/kg respectively.The 3,4-dichlorophenyl analogue (32) is effective at a dose of 30 mg/kg. 2-(3,5-Bistrifluoromethylphenyl)hydrazinothiazoline (51) and the corresponding dihydrothiazine (63) show a weaker activity.The biological profile of C 2696-Go has been investigated in detail.It appears to prevent implantation by its antiuterotropic activity and ability to inhibit desiduoma formation.

Process for producing 3-anilino-5-pyrazolones

A process for producing a 3-anilino-5-pyrazolone which comprises reacting a β-anilino-β-alkoxy-acrylate with a hydrazine in the presence of a compound having a pKa of about 8 up to about 14.