39513-19-4

Usage

Uses

Production of dyes, pigments, and pharmaceuticals

Physical properties

Light-sensitive, colorless solid

Solubility

Soluble in organic solvents

Health hazards

Skin irritant, eye and respiratory irritation

Safety

Considered hazardous material, handle with appropriate safety measures

Upstream product

• 4600-08-2 4,N-dimethyl-2-nitroaniline 
• 7647-01-0 hydrogenchloride 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 616-38-6 carbonic acid dimethyl ester 
• 446-11-7 4-fluoro-3-nitrotoluene 
• 3968-10-3 BTB₀₁₄₃₄ 
• 89-62-3 4-methyl-2-nitroaniline 
• 7439-89-6 iron 
• 108-44-1 1-amino-3-methylbenzene 
• 89-60-1 1-chloro-4-methyl-2-nitro-benzene 
• 19871-42-2 toluene-4-sulfonic acid-(4,N-dimethyl-2-nitro-anilide) 
• 103-89-9 4-Methylacetanilide 

Downstream Products

• 5618-84-8 7,10-dimethyl-10H-benzo[g]pteridine-2,4-dione 
• 24780-84-5 1,2,5-Trimethyl-Benzimidazol 
• 93732-68-4 2-(1,5-dimethyl-1H-benzoimidazol-2-yl)-phenol 
• 149530-79-0 5-methylbenzimidazoline-2-thione 
• 39513-28-5 1,5-dimethyl-1,3-dihydro-benzoimidazol-2-one 
• 10394-35-1 1,5-dimethylbenzimidazole 
• 4600-28-6 1,5-Dimethyl-2-phenyl-2,3-dihydro-1H-1,3,2-benzodiaza-phosphol-2-sulfid 
• 22525-69-5 8-methylalloxazine 
• 92473-54-6 1,6-Dimethyl-1,4-dihydro-quinoxaline-2,3-dione 
• 65-45-2 salicylamide 
• 690231-89-1 2-chloro-N-(5-methyl-2-methylamino-phenyl)-5-nitro-benzamide 
• 423755-05-9 2-(2-chloro-5-nitro-phenyl)-1,5-dimethyl-1H-benzoimidazole 
• 39860-12-3 C₉H₁₁N₃ 
• 39860-12-3 2-Amino-1,5-dimethyl-benzimidazol 

Relevant academic research and scientific papers

Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes

CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.

Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines

The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.

Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles

Upon irradiation, cyclic imines containing o-amido groups are shown to produce reactive intermediates, amino azaxylylenes, which undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex N,O-heterocycles having an additional spiro-connected nitrogen heterocyclic moiety. Modular assembly of the photoprecursors allows expeditious increase of the complexity of the target poly-heterocyclic scaffolds with a minimal number of experimentally simple reaction steps. The photocyclization and subsequent postphotochemical transformations are accompanied by an increase of Lovering's fsp3 factor, thus producing unprecedented three-dimensional molecular architectures, and offering extended sampling of chemical space. Rings in three dimensions: Cyclic imines containing an o-amido group undergo excited-state intramolecular proton transfer to generate amino azaxylylenes. The amino azaxylylenes undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex heterocyclic three-dimensional molecular architectures.

Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action

In this report we describe 2-iminobenzimidazole (IBI) analogs, identified during the course of a phenotypic high-throughput screening campaign, as novel hepatitis C virus (HCV) inhibitors. A series of IBI derivatives was synthesized and evaluated for their inhibitory activity against infectious HCV. Among the IBIs derivatives studied in this work, we identified promising compounds with high antiviral efficacy, high selectivity index and good microsomal stability. Noteworthy, the IBI series exhibited inhibitory activity on early and late steps of the viral cycle, but not in the HCV replicon system demonstrating a mechanism of action distinct from clinical-stage and approved anti-HCV drugs. Overall, our results suggest that IBIs are predestinated for further exploration as lead compounds for novel HCV interventions.

Bicyclic Benzimidazole Compounds and Their Use as Metabotropic Glutamate Receptor Potentiators

Compounds of Formula I: wherein A, B, D, L, R1, R2, R3, R4, m, and n are as defined for Formula I in the description. The invention also relates to processes for the preparation of the compounds and to new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and to the use of the compounds in therapy.

Discovery of small molecule benzimidazole antagonists of the chemokine receptor CXCR3

High-throughput screening identified a low molecular weight antagonist of CXCR3 displaying micromolar activity in a membrane filtration-binding assay. Systematic modification of the benzimidazole core and tethered acetophenone moiety established tractable SAR of analogs with improved physicochemical properties and sub-micromolar activity across both human and murine receptors.

Highly selective zeolite-catalysed mono-N-alkylation of arylenediamines by dialkyl carbonates

Arylenediamines are mono-N-alkylated by dialkyl carbonates in the presence of NaY zeolite catalyst in a regioselective and nontoxic process.

Synthesis and SAR of 2-arylbenzoxazoles, benzothiazoles and benzimidazoles as inhibitors of lysophosphatidic acid acyltransferase-β

2-Arylbenzoxazoles, benzothiazoles and benzimidazoles were identified as new classes of potent, isoform specific inhibitors of lysophosphatidic acid acyltransferase-β (LPAAT-β). Effects of selected inhibitors on proliferation of tumor cells in vitro were investigated.

Benzoxazole LPAAT-B inhibitors and uses thereof

The invention relates to benzoxazoles and the use thereof to inhibit lysophosphatidic acid acyltransferase β (LPAAT-β) activity. The invention further relates to methods of treating cancer using said benzoxazoles. The invention also relates to methods for screening for LPAAT-β activity.

Linear free energy substitutent effect on flavin redox chemistry

A systematic study on the effect of various substituents at the 7- and/or 8-position on the redox properties of isoalloxazines (flavins) is reported. The redox properties of these flavin derivatives were studied by cyclic voltammetry in 100 mM, pH 7.4 HEPES and 200 mM, pH 10 borate buffers. The magnitude and direction of the effect was dependent on the nature and location of the substituent. The redox potentials of the substituted flavins were correlated with the Hammett σ value of the substituents.