28458-68-6

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
1-N-tert-Butylbenzene-1,2-diamine is used as a building block for the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and steric hindrance from the tert-butyl group make it a valuable component in the development of new drugs and agricultural chemicals.
Used in Epoxy Resin Curing:
1-N-tert-Butylbenzene-1,2-diamine is used as a curing agent for epoxy resins. Its ability to react with the epoxy groups in the resin contributes to the formation of a cross-linked network, enhancing the mechanical properties and thermal stability of the cured material.
Used in Organic Reactions as a Catalyst:
1-N-tert-Butylbenzene-1,2-diamine is employed as a catalyst in various organic reactions. Its presence can accelerate reaction rates, improve selectivity, and facilitate the formation of desired products, making it a useful tool in organic synthesis and process optimization.
Used in Research Applications:
1-N-tert-Butylbenzene-1,2-diamine is utilized in research settings for the investigation of new chemical reactions, the development of novel synthetic methods, and the study of reaction mechanisms. Its unique properties and reactivity make it a valuable compound for advancing scientific knowledge and discovering new applications.

Upstream product

• 17877-23-5 triisopropylsilanol 
• 791-31-1 triphenylhydroxysilane 
• 88589-59-7 bis(2,4,6-trimethylphenyl)silanol 
• 75-64-9 tert-butylamine 
• 1493-27-2 ortho-nitrofluorobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 28458-45-9 N-(tert-butyl)-2-nitroaniline 

Downstream Products

• 76060-04-3 2-(2-nitrophenyl)-1-(t-butyl)-2,3-dihydrobenzimidazole 
• 76060-10-1 2-(2-aminophenyl)-1-(t-butyl)benzimidazole 
• 76060-11-2 2-(2-azidophenyl)-1-(t-butyl)benzimidazole 
• 76060-07-6 2-(2-nitrophenyl)-1-(t-butyl)benzimidazole 
• 1189055-89-7 1-tert-butyl-2-(N-phenylamino)benzimidazole 
• 17582-96-6 1-(tert-butyl)-1H-benzimidazole 
• 180207-78-7 (3,5-Dimethyl-piperazin-1-yl)-[3-(4-methoxy-phenyl)-4H-imidazo[1,5-a]quinoxalin-5-yl]-methanone 

Relevant academic research and scientific papers

Molecular Scissors for Tailor-Made Modification of Siloxane Scaffolds

The controlled design of functional oligosiloxanes is an important topic in current research. A consecutive Si?O?Si bond cleavage/formation using siloxanes that are substituted with 1,2-diaminobenzene derivatives acting as molecular scissors is presented.

Biomimetic alloxan-catalyzed intramolecular redox reaction with O2: One-pot atom-economic synthesis of sulfinyl-functionalized benzimidazoles

Given the necessity of sacrificial reductants in various biomimetic aerobic oxygenations, alloxan-catalyzed aerobic redox system for one-pot atom-economic synthesis of sulfinyl-functionalized benzimidazoles was developed by ingeniously binding both the substrate sulfide and sacrificial reductant. This mild and transition-metal-free protocol undergoes two oxidations without additional sacrificial reagents, except for the environmentally benign molecular oxygen.

TREX1 INHIBITORS AND USES THEREOF

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds for inhibiting three prime repair exonuclease 1 ("TREX1").

CRBN LIGANDS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.

Synthetic, structural, and computational investigations of N-alkyl benzo-2,1,3-selenadiazolium iodides and their supramolecular aggregates

Despite their versatility, the application of telluradiazoles as supramolecular building blocks is considerably constrained by their sensitivity to moisture. Albeit more robust, their selenium analogues form weaker supramolecular interactions. These, however, are enhanced when one nitrogen atom is bonded to an alkyl group. Here we investigate general methods for the synthesis of such derivatives. Methyl, iso-propyl and tert-butyl benzo-2,1,3-selenadiazolium cations were prepared by direct alkylation or cyclo-condensation of the alkyl-phenylenediamine with selenous acid. While the former reaction only proceeds with the primary and tertiary alkyl iodides, the latter is very efficient. Difficulties reported in earlier literature are attributable to the formation of adducts of benzoselenadiazole with its alkylated cations and side reactions initiated by aerobic oxidation of iodide. However, the cations themselves are resilient to oxidation and stable in acidic to neutral aqueous medium. X-ray crystallography was used in the identification and characterization of the following compounds: [C6H4N2(R)Se]+X-, (R = CH(CH3)2, C(CH3)3; X = I-, I3-], [C6H4N2(CH3)Se]+I-, and [C6H4N2Se][C6H4N2(CH3)Se]2I2. Formation of Se?N secondary bonding interactions (chalcogen bonds) was only observed in the last structure as anion binding to selenium is a strong competitor. The relative strengths of those forces and the structural preferences they enforce were assessed with DFT-D3 calculations supplemented by AIM analysis of the electron density.

Protic N-Heterocyclic Germylenes and Stannylenes: Synthesis and Reactivity

The monoalkylated or monoarylated o-phenylenediamines 1a-d (1a, R = t-Bu; 1b, R = adamantyl; 1c, R = phenyl; 1d, R = mesityl) react via transamination with Ge[N(SiMe3)2]2 or Sn[N(SiMe3)2]2 to give the protic benzimidazolin-2-germylenes 2a-d or the benzimidazolin-2-stannylenes 3a,b. Germylenes 2a,b can be deprotonated to give the salts Na-4a and Na-4b, each containing an anionic N-deprotonated N-heterocyclic germylene. The protic stannylenes 3a,b react with NaH presumably via reduction of the tin(II) center by the deprotonated electron-rich o-phenylenediamine ligand and release of elemental tin. To prevent this reduction, the electron-poor N-H,N′-H-5,6-dibromobenzimidazolin-2-stannylene (5) was prepared and successfully N-deprotonated to give an anionic stannylene in Na-6. The molecular structures of 2a, 3a, and Na-4a were established by X-ray diffraction studies. (Chemical Presented).

Imidoyl dichlorides as new reagents for the rapid formation of 2-aminobenzimidazoles and related azoles

The development of a reagent for the efficient synthesis of five- and six-membered azoles at room temperature is proposed. A variety of substituted 2-aminobenzimidazoles are synthesized in good to excellent yields. The ability to incorporate various protecting groups makes the imidoyl dichloride reagent amenable to a large number of syntheses. The reagent is applied to the total synthesis of the 2-aminobenzimidazole containing carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), from 2-chloro-3-nitropyridine in >60% yield in 6 steps.

GSK-3BETA INHIBITOR

For the purpose of providing a GSK-3β inhibitor containing a 2-aminopyridine compound or a salt thereof or a prodrug thereof useful as an agent for the prophylaxis or treatment of a GSK-3β-related pathology or disease, the present invention provides a GSK-3β inhibitor containing a compound represented by the formula (IA): wherein each symbol is as defined in the specification. or a salt thereof or a prodrug thereof.

Syntheses and15N NMR Spectra of Iminodiaziridines - Ring-Expansions of 1-Aryl-3-iminodiaziridines to 1H- and 3aH-Benzimidazoles, 2H-Indazoles, and 5H-Dibenzo[d,f] [1,3]diazepines

Iminodiaziridines are synthesized, by (i) 1,3-dehydrochlorination with potassium, teri-butoxide of N-chloroguanidines, generated in situ from. N,N′,N″-substituted guanidines with tert-butyl hypochlorite, and (ii) base-mediated 1,3-elimination of sulfuric acid from N,N',N″- substituted hydroxyguanidine O-sulfonic acids. At elevated temperatures, (alkylimino)diaziridines undergo valence isomerization by 1,3shift, [2+1] cycloelimination to afford isocyanides and diazenes, and ring-opening elimination to yield alkylideneguanidines. N′-Aryl-N-hydroxyguanidine O-sulfonic acids furnish (N-arylimino)diaziridines, but no 1-aryl-3- iminodiaziridines, instead giving rearranged isomere. Precursors containing perdeuterated feri-butyl groups give rearranged products that show complete scrambling. This indicates that l-aryl-3iminodiaziridines are intermediates that undergo very rapid I degenerate valence isomerization. Provided that the ortho aryl positions are substituted, high yields of (arylimino)diaziridines are obtained, along with 2-imino-2,3-dihydro-3aHbenzimidazoles, Otherwise, 2-amino-lH-benzimidazoles and strongly fluorescent 3-amino-2H-indazoles, originating from rearrangements of the elusive l-aryl-3-iminodiaziridines, predominate. N',N″-Diaryl-N-hydroxyguanidine O-sulfonic acids give only rearranged products: a 2-amino-1H-benzimidazole and a 6-amino-5H-dibenzo[d,f][1. 3]diazepine if aryl = phenyl, or a 2-imino-2,3-dihydro-3aH-benzimidazole if aryl = mesityl. 3aH-Benzimidazoles slowly dimerize through Diels-Alder reactions. 15N NMR signals were assigned, to the syn and anti ring nitrogen atoms of iminodiaziridines with the help of a combination of homonuclear NOE and HNHMBC or HN-gHMBC experiments.

1- Or 3-(3-amino-2-hydroxy-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2- ones: Potent, selective, and orally efficacious norepinephrine reuptake inhibitors

Sequential structural modifications of the aryloxypropanamine template (e.g., atomoxetine, 2) led to a novel series of 1-(3-amino-2-hydroxy-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors (NRIs). In general, this series of compounds potently blocked the human norepinephrine transporter (hNET) while exhibiting selectivity at hNET against both the human serotonin (hSERT) and dopamine transporters (hDAT). Numerous compounds (e.g., 19-22) had low nonamolar hNET potency with IC 50 values of 7-10 nM and excellent selectivity (>500 fold) at hNET over hSERT and hDAT. Several compounds, such as 20 and 22, were tested in a telemetric rat model of ovariectomized-induced thermoregulatory dysfunction and were efficacious at oral doses of 3 mg/kg in reducing the tail skin temperature. In addition, compound 20 was also studied in the rat hot plate and spinal nerve ligation (SNL) models of acute and neuropathic pain, respectively, and was orally efficacious at doses of 3-10 mg/kg.