2192-33-8

Upstream product

• 87-62-7 2,6-dimethylaniline 

Downstream Products

• 632-46-2 2,6-dimethylbenzoic acid 
• 2198-53-0 N-(2,6-dimethylphenyl)acetamide 
• 73368-14-6 2,6-Dimethylbenzoic anhydride 
• 86436-78-4 2,6-dimethylphenyl tellurocyanide 
• 86436-76-2 C₁₆H₁₈Te 
• 18109-39-2 N-(2,6-diimethylphenyl)benzamide 
• 2905-17-1 bis(2,6-dimethylphenyl)disulfide 
• 443-88-9 2-fluoro-m-xylene 
• 325141-72-8 2-(2,6-bismethylphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane 
• 170502-72-4 2-Fluoro-isophthaldialdehyde 
• 106776-16-3 1,3-Bis(dibromomethyl)-2-fluorobenzene 
• 81028-33-3 (C₅H₅)Re(CO)2(N₂C₆H₃(CH₃)2)⁽¹⁺⁾*BF₄^(1-)=(C₅H₅)Re(CO)2(N₂C₆H₃(CH₃)2)BF₄ 
• 116164-12-6 N-(tert-butyl)-N'-(2,6-dimethylphenyl)diazene 
• 180783-48-6 2,6-dimethyl-1-(phenylethynyl)benzene 

Relevant academic research and scientific papers

Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches

We report a modular approach toward novel arylazotriazole photoswitches and their photophysical characterization. Addition of lithiated TIPS-acetylene to aryldiazonium tetrafluoroborate salts gives a wide range of azoacetylenes, constituting an underexplored class of stable intermediates.In situdesilylation transiently leads to terminal arylazoacetylenes that undergo copper-catalyzed cycloadditions (CuAAC) with a diverse collection of organoazides. These include complex molecules derived from natural products or drugs, such as colchicine, taxol, tamiflu, and arachidonic acid. The arylazotriazoles display near-quantitative photoisomerization and long thermalZ-half-lives. Using the method, we introduce for the first time the design and synthesis of a diacetylene platform. It permits implementation of consecutive and diversity-oriented approaches linking two different conjugants to independently addressable acetylenes within a common photoswitchable azotriazole. This is showcased in the synthesis of several photoswitchable conjugates, with potential applications as photoPROTACs and biotin conjugates.

Preparation of N-Arylquinazolinium Salts via a Cascade Approach

An easy manipulation method for the preparation of N-arylquinazolinium salts is described from readily available aryldiazonium salts, nitriles, and 2-aminoarylketones in a one-pot operation. This method relies on the in situ generation of the N-arylnitrilium intermediate from the reaction of aryldiazonium salt with nitrile, which undergoes amination/cascade cyclization/aromatization, leading to N-arylquinazolinium salts in excellent yields. Nucleophilic addition of alkoxide to these N-arylquinazolinium salts provides functionalized dihydro-N-arylquinazoline.

Inhibition of the Cysteine Protease Human Cathepsin L by Triazine Nitriles: Amide???Heteroarene π-Stacking Interactions and Chalcogen Bonding in the S3 Pocket

We report an extensive “heteroarene scan” of triazine nitrile ligands of the cysteine protease human cathepsin L (hCatL) to investigate π-stacking on the peptide amide bond Gly67–Gly68 at the entrance of the S3 pocket. This heteroarene???peptide bond stacking was supported by a co-crystal structure of an imidazopyridine ligand with hCatL. Inhibitory constants (Ki) are strongly influenced by the diverse nature of the heterocycles and specific interactions with the local environment of the S3 pocket. Binding affinities vary by three orders of magnitude. All heteroaromatic ligands feature enhanced binding by comparison with hydrocarbon analogues. Predicted energetic contributions from the orientation of the local dipole moments of heteroarene and peptide bond could not be confirmed. Binding of benzothienyl (Ki=4 nm) and benzothiazolyl (Ki=17 nm) ligands was enhanced by intermolecular C?S???O=C interactions (chalcogen bonding) with the backbone C=O of Asn66 in the S3 pocket. The ligands were also tested for the related enzyme rhodesain.

Synthesis and DNA-cleaving activity of a series of substituted arenediazonium ions

We investigated the reactions of substituted aryl radicals and aryl cations derived from arenediazonium ions and their ability to cause cleavage of supercoiled DNA and their tendency toward free radical or cation formation in the presence and absent of co

A Fluorine-Containing Cryptand for the Complexation of Anions and the Utility of 19F NMR Spectroscopy for the Determination of Host-Guest Association

The first fluorine-containing cryptand F3-TREN 4 for the complexation of anions was prepared in the 3 + 2-condensation reaction of 2-fluoro-1,3-phthalaldehyde 3 with tris(2-aminoethyl)amine and subsequent reduction with NaBH4.Upon incorporation of anionic guests 4*6HClO4 experiences shifts of its 19F NMR resonances and thus demonstrates the advantages of studying host-guest association by 19F NMR spectroscopy. - Keywords: Macrocycles, 19F NMR Spectra, Fluorine, Anion Complexation

Influence of Steric and Electronic Effects on the Binding of Arenediazonium Cations to 18-Crown-6 in Methanol at 25 deg C

Log K, ΔH, and TΔS values for the interaction of several arenediazonium salts with 18-crown-6 were determined in methanol at 25 deg C by the calorimetric titration technique.The complex of benzenediazonium cation with 18-crown-6 is enthalpy stabilized with log K = 2.50.Substitution of a methyl group onto the ortho position(s) of benzenediazonium cation results in a total loss of complex stability.Substitution of various groups onto the para position results in changes in complex stability according to the electronic effect exerted in the diazonium moiety.A linear Hammett relationship (ρ = 0.65) was found between log K and ?+p values associated with the para substituent.