14213-00-4

Usage

Physical properties

2,4,6-trimethylphenyl azide is a yellow crystalline solid.

Chemical reactivity

The compound is highly reactive and can undergo photochemical reactions, particularly in the process of photoaffinity labeling.

Uses

2,4,6-trimethylphenyl azide is commonly used in organic synthesis and as a precursor to other chemical compounds. It is also used as a starting material for the synthesis of various pharmaceuticals and agrochemicals.

Safety precautions

The compound is potentially explosive when heated or exposed to shock, so it should be handled with caution.

Upstream product

• 88-05-1 2,4,6-trimethylaniline 
• 108-67-8 1,3,5-trimethyl-benzene 
• 197245-87-7 (2,4,6-trimethylphenyl)(3’-methylphenyl)iodonium triflate 
• 5980-97-2 mesitylboronic acid 
• 4028-63-1 iodomesitylene 
• 171364-84-4 2-(2,4,6-trimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 

Downstream Products

• 132093-26-6 N-mesityl-1,2-disila-1,1,2,2-tetramesitylaziridine 
• 132068-15-6 1,4,4,5,5-Pentakis-(2,4,6-trimethyl-phenyl)-4,5-dihydro-1H-[1,2,3,4,5]triazadisilole 
• 86133-53-1 [(2,4,6-trimethylphenyl)imino](triphenyl)phosphorane 
• 2325-27-1 N-phenyltriphenyliminophosphorane 
• 88-05-1 2,4,6-trimethylaniline 
• 5692-66-0 2,2',4,4',6,6'-hexamethylazobenzene 
• 213013-05-9 methyl 1-(2,4,6-trimethylphenyl)-1H-1,2,3-triazole-4-carboxylate 
• 132775-06-5 2,2,4,4-tetramesityl-1,3,2,4-dioxadigermetane 
• 34143-89-0 2,4,6-trimethyl-N-(phenylmethylene)benzenamine 
• 124862-50-6 {N-mesityldimesitylgermaimine}n 
• 129016-32-6 (C₆H₂(CH₃)3)2GeN(C₆H₂(CH₃)3)NNN(C₆H₂(CH₃)3) 
• 134311-22-1 ((2,4,6-tris(trifluoromethyl)benzene)2Sn)2N(mesityl) 
• 153092-89-8 bis{bis(trimethylsilyl)amino}{(2,4,6-trimethylphenyl)amino}-2-pyridylstannane 
• 163929-87-1 [Mo(N(C(⁽²⁾H₃C)2CH₃)((CH₃)2C₆H₃))3N] 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole triazole derivatives as potent TRPV1 antagonists

Reported herein is the design, synthesis, and pharmacologic evaluation of a class of TRPV1 antagonists constructed on 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole as A-region and triazole as B-region. The SAR analysis indicated that 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole analogues displayed excellent antagonism of hTRPV1 activation by capsaicin and showed better potency compared to the corresponding dihydroindole analogues. Optimization of this design led to the eventual identification of 2-((1-(2-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (6g), a potent TRPV1 antagonist. In vitro, using cells expressing recombinant human TRPV1 channels, 6g displayed potent antagonism activated by capsaicin (IC50 = 0.075 μM) and only partially blocked acid activation of TRPV1. In vivo, 6g exhibited good efficacy in capsaicin-induced and heat-induced pain models and had almost no hyperthermia side-effect. Furthermore, pharmacokinetic studies revealed that compound 6g had a superior oral exposure after oral administration in rats. To understand its binding interactions with the receptor, the docking study of 6g was performed in rTRPV1 model and showed an excellent fit to the binding site. On the basis of its superior profiles, 6g could be considered as the lead candidate for the further development of antinociceptive drugs.

Triazole based cobalt catalyst for CO2 insertion into epoxide at ambient pressure

Over the past decades, a lot of efforts have been made for the fixation of carbon dioxide (CO2) into epoxide for the synthesis of industrially important cyclic carbonates. Here, a cobalt(II) complex based on triazole, namely Co(II)-1,2,3-1H-triazole-4-carboxylate, was synthesized, fully characterized by FTIR, NMR, mass spectrometry, and single crystal X-ray diffraction, and used as a catalyst for the cycloaddition of CO2 to epoxides. The catalytic studies demonstrated that the catalyst is highly active for the CO2 fixation, with high turnover number (TON, 85 × 103) even without the use of solvent and at ambient pressure (1 bar) to produce a variety of different cyclic carbonates depending on the epoxide. Remarkably, the catalyst was used continuously further by the addition of a fresh amount of the substrate within the same reaction mixture for at least five successive reaction cycles without any loss in the catalytic activity.

DBU-promoted Cu(OAc)2·H2O-catalysed coupling reactions of aryl iodides and sodium azide

An efficient and simple protocol for the synthesis of aryl azides by the coupling of aryl iodides with sodium azide, in good to excellent yields in DMSO at 95°C under catalysis by Cu(OAc)2·H2O and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), has been established. The optimised loadings of Cu(OAc)2·H2O and DBU were 10 mol% and 15 mol% respectively.

Water Oxidation at Neutral pH using a Highly Active Copper-Based Electrocatalyst

The sluggish kinetics of the oxygen evolution reaction (OER) at the anode severely limit hydrogen production at the cathode in water splitting systems. Although electrocatalytic systems based on cheap and earth-abundant copper catalysts have shown promise

An Iron-Mesoionic Carbene Complex for Catalytic Intramolecular C-H Amination Utilizing Organic Azides

The synthesis of N-heterocycles is of paramount importance for the pharmaceutical industry. They are often synthesized through atom economic and environmentally unfriendly methods, generating significant waste. A less explored, but greener, alternative is

Discovery of a Series of Theophylline Derivatives Containing 1,2,3-Triazole for Treatment of Non-Small Cell Lung Cancer

Chemotherapy is the most common clinical treatment for non-small cell lung cancer (NSCLC), but low efficiency and high toxicity of current chemotherapy drugs limit their clinical application. Therefore, it is urgent to develop hypotoxic and efficient chemotherapy drugs. Theophylline, a natural compound, is safe and easy to get, and it can be used as a modified scaffold structure and hold huge potential for developing safe and efficient antitumor drugs. Herein, we linked theophylline with different azide compounds to synthesize a new type of 1,2,3-triazole ring-containing theophylline derivatives. We found that some theophylline1,2,3-triazole compounds showed a good tumor-suppressive efficacy. Especially, derivative d17 showed strong antiproliferative activity against a variety of cancer cells in vitro, including H460, A549, A2780, LOVO, MB-231, MCF-7, OVCAR3, SW480, and PC-9. It is worth noting that the two NSCLC cell lines H460 H and A549 are sensitive to compound d17 particularly, with IC50 of 5.929 ± 0.97?μM and 6.76 ± 0.25?μM, respectively. Compound d17 can significantly induce cell apoptosis by increasing the ratio of apoptotic protein Bax/Bcl-2 by downregulating the expression of phosphorylated Akt protein, and it has little toxicity to normal hepatocyte cells LO2 at therapeutic concentrations. These data indicate that these theophylline acetic acid-1,2,3-triazole derivatives may be potential drug candidates for anti-NSCLC and are worthy of further study.

Cycloaddition Reactions of Azides and Electron-Deficient Alkenes in Deep Eutectic Solvents: Pyrazolines, Aziridines and Other Surprises

The reaction of organic azides and electron-deficient alkenes was investigated in a deep eutectic solvents. A series of highly substituted 2-pyrazolines was successfully isolated and their formation rationalised by DFT calculations. The critical effect of substitution was also explored; even relatively small changes in the cycloaddition partners led to completely different reaction outcomes and triazolines, triazoles or enaminones can be formed as major products depending on the alkene employed. (Figure presented.).

Identification of highly potent and selective Cdc25 protein phosphatases inhibitors from miniaturization click-chemistry-based combinatorial libraries

Cell division cycle 25 (Cdc25) protein phosphatases play key roles in the transition between the cell cycle phases and their association with various cancers has been widely proven, which makes them ideal targets for anti-cancer treatment. Though several Cdc25 inhibitors have been developed, most of them displayed low activity and poor subtype selectivity. Therefore, it is extremely important to discover novel small molecule inhibitors with potent activities and significant selectivity for Cdc25 subtypes, not only served as drugs to treat cancer but also to probe its mechanism in transitions. In this study, miniaturized parallel click chemistry synthesis via CuAAC reaction followed by in situ biological screening were used to discover selective Cdc25 inhibitors. The bioassay results showed that compound M2N12 proved to be the most potent Cdc25 inhibitor, which also act as a highly selective Cdc25C inhibitor and was about 9-fold potent than that of NSC 663284. Moreover, M2N12 showed remarkable anti-growth activity against the KB-VIN cell line, equivalent to that of PXL and NSC 663284. An all-atom molecular dynamics (MD) simulation approach was further employed to probe the significant selectivity of M2N12 for Cdc25C relative to its structural homologs Cdc25A and Cdc25B. Overall, above results make M2N12 a promising lead compound for further investigation and structural modification.

The impact of cation structure upon the acidity of triazolium salts in dimethyl sulfoxide

A series of triazolium salts, selected for their varying electronic and steric properties, were prepared and their pKa values were determined in DMSO at 25 °C using the bracketing indicator method. The effect of each systematic structural variation upon the acidity of the triazolium cation has been considered, in particular examining the effects of systematically altering electronic properties, quantified through the use of Hammett σ parameters. The first pKa value for an azolium salt that generates a mesionic carbene is also reported. These new data allow for the selection of appropriate bases for the deprotonation of such triazolium salts and the potential to correlate the pKa values determined herein with the nucleophilicity of the corresponding carbenes.

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.