10173-53-2

Basic information

• Product Name: 2-(6-methyl-1H-benzimidazol-2-yl)aniline
• CAS NO: 10173-53-2
• Molecular Formula: C₁₄H₁₃N₃
• Molecular Weight: 223.2731
• Mol File: 10173-53-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 469°C at 760 mmHg
• Flash Point: 268.7°C
• Density: 1.247g/cm³
• Vapor Pressure: 5.69E-09mmHg at 25°C
• Refractive Index: 1.714
• CAS DataBase Reference: 2-(6-methyl-1H-benzimidazol-2-yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(6-methyl-1H-benzimidazol-2-yl)aniline(10173-53-2)
• EPA Substance Registry System: 2-(6-methyl-1H-benzimidazol-2-yl)aniline(10173-53-2)

Safety Data

• Hazardous Substances Data: 10173-53-2(Hazardous Substances Data)

Usage

Chemical class

Benzimidazole derivatives

Structure

Benzimidazole ring fused with an aniline group, with a methyl group attached to the benzimidazole ring at the 6-position

Potential applications

Pharmaceutical research and drug development

Biological activities

May exhibit potential pharmacological properties

Synthesis

Can act as a building block for the synthesis of biologically active compounds

Further research

Exploration of this compound and its derivatives may contribute to the development of new drugs and therapeutic agents.

Upstream product

• 636-24-8 4-Methyl-benzene-1,2-diamine; hydrochloride 
• 28144-70-9 anthranilic acid amide 
• 7647-01-0 hydrogenchloride 
• 92164-93-7 2-nitro-benzoic acid-(4-methyl-2-nitro-anilide) 
• 216985-56-7 anthranilic acid-(2-amino-4-methyl-anilide) 
• 133721-90-1 sodium hydroxy(2-nitrophenyl)methanesulfonate 
• 552-89-6 2-nitro-benzaldehyde 
• 118-92-3 anthranilic acid 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 578-46-1 5-methyl-2-nitroaniline 
• 89-62-3 4-methyl-2-nitroaniline 
• 610-14-0 2-nitrobenzyl chloride 
• 118-48-9 isatoic anhydride 

Downstream Products

• 1334316-69-6 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(2-chlorophenyl)thiazolidin-4-one 
• 1334316-70-9 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(4-chlorophenyl)thiazolidin-4-one 
• 1334316-71-0 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(2,4-dichlorophenyl)thiazolidin-4-one 
• 1334316-72-1 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(4-fluorophenyl)thiazolidin-4-one 
• 1334316-73-2 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(3-hydroxyphenyl)thiazolidin-4-one 
• 1334316-74-3 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(4-hydroxyphenyl)thiazolidin-4-one 
• 1334316-75-4 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(3,4-dimethoxyphenyl)thiazolidin-4-one 
• 1334316-77-6 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(2-nitrophenyl)thiazolidin-4-one 
• 1334316-78-7 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(3-nitrophenyl)thiazolidin-4-one 
• 1334316-79-8 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(4-nitrophenyl)thiazolidin-4-one 
• 1334316-80-1 3-(2-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-2-(2,4-dinitrophenyl)thiazolidin-4-one 
• 1391001-46-9 C₂₁H₁₆ClN₃ 
• 1391001-45-8 C₂₁H₁₆ClN₃ 
• 1391001-44-7 C₂₁H₁₅Cl₂N₃ 

Relevant articles and documents

Synthesis and biological evaluation of substituted N-(2-(1H-benzo[d]imidazol-2-yl)phenyl)cinnamides as tubulin polymerization inhibitors

A new series of N-(2-(1H-benzo[d]imidazol-2-yl)phenyl) cinnamides was prepared and evaluated for their in vitro cytotoxic activity using various cancer cell lines viz. A549 (human non-small cell lung cancer), MDA-MB-231 (human triple negative breast cancer), B16-F10 (mouse melanoma), BT-474 (human breast cancer), and 4 T1 (mouse triple negative breast cancer). In the series of tested compounds, 12h showed potent cytotoxic activity against non-small cell lung cancer cell line with IC50 value of 0.29 ± 0.02 μM. The cytoxicity of most potent compound 12h was also tested on NRK-52E (normal rat kidney epithelial cell line) and showed less cytotoxicity compared to cancer cells. Tubulin polymerization assay indicated that the compound 12h was able to impede the cell division by inhibiting tubulin polymerization. Moreover, molecular docking study also suggested the binding of 12h at the colchicine-binding site of the tubulin protein. Cell cycle analysis revealed that the compound 12h arrests G2/M phase. In addition, 12h induced apoptosis in A549 cell lines was evaluated by various staining studies like acridine orange, DAPI, analysis of mitochondrial membrane potential, annexin V-FITC, and DCFDA assays.

Nickel-Catalyzed Aerobic Oxidative Isocyanide Insertion: Access to Benzimidazoquinazoline Derivatives via a Sequential Double Annulation Cascade (SDAC) Strategy

An efficient protocol for the synthesis of quinazoline derivatives through nickel-catalyzed ligand-/base-free oxidative isocyanide insertion under aerobic conditions with intramolecular bis-amine nucleophiles has been developed. A one-pot sequential double annulation cascade (SDAC) strategy involving an opening of isatoic anhydride and annulation to benzimidazole and further nickel-catalyzed intramolecular isocyanide insertion has also been demonstrated. The method is operationally simple to implement with a wide variety of substrates and represents a new approach for multiple C-N bond formations. The methodology has been successfully applied to the syntheses of hitherto unreported imidazo-fused benzimidazoquinazolines via a deprotection-GBB reaction sequence. Further, a florescence study reveals the potential of the present strategy for the discovery of highly fluorescent probes.

Efficient method for the synthesis of benzimidazoquinazoline derivatives with three-point diversity

An efficient strategy for the preparation of a novel heterocyclic ring system of benzimidazoquinazolines with three-point diversity has been described. The compounds were obtained by treating o-phenylene diamines with o-nitrobenzaldehyde to give benzimidazoles, followed by reduction of the nitro group to give an amine. Derivatization of the resulting amine with isothiocyanates followed by in situ cyclodesulfurization at rt furnished the title compounds in high yields and purities. Copyright Taylor & Francis Group, LLC.