29528-27-6

Basic information

• Product Name: 2-(1H-IMIDAZOL-4-YL)-PHENYLAMINE
• Synonyms: 2-(1H-IMIDAZOL-4-YL)-PHENYLAMINE;2-(1H-IMidazol-4-yl)aniline;2-(1H-imidazol-5-yl)aniline
• CAS NO: 29528-27-6
• Molecular Formula: C₉H₉N₃
• Molecular Weight: 159.18786
• Mol File: 29528-27-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(1H-IMIDAZOL-4-YL)-PHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1H-IMIDAZOL-4-YL)-PHENYLAMINE(29528-27-6)
• EPA Substance Registry System: 2-(1H-IMIDAZOL-4-YL)-PHENYLAMINE(29528-27-6)

Safety Data

• Hazardous Substances Data: 29528-27-6(Hazardous Substances Data)

Usage

Type of compound

Aromatic amine

Structure

Imidazole ring with a phenyl group attached to its nitrogen atom

Usage in industry

Building block for the synthesis of various organic compounds and drug molecules

Potential applications

Antifungal, antiviral, and anticancer drugs

Mechanism of action

Ability to interact with biological targets, such as enzymes and receptors

Additional uses

Synthesis of fluorescent dyes, polymers, and materials for electronics and optoelectronics

Safety precautions

Toxic and may cause irritation to skin, eyes, and respiratory system

Upstream product

• 51746-89-5 4-(2-Nitro-phenyl)-1H-imidazole 
• 51746-89-5 5-(2-nitrophenyl)-1H-imidazole 
• 6851-99-6 2-bromo-1-(2-nitrophenyl)ethanone 

Downstream Products

• 1300729-07-0 (E)-N-benzylidene-2-(1H-imidazol-5-yl)aniline 
• 1300729-01-4 N-(2-(1H-imidazol-4-yl)phenyl)acetamide 
• 130209-88-0 5-(2-aminophenyl)-3H-imidazole-dihydrochloride 

Relevant articles and documents

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

The heme enzyme indoleamine 2,3-dioxygenase 1 (IDO1) plays an essential role in immunity, neuronal function, and aging through catalysis of the rate-limiting step in the kynurenine pathway of tryptophan metabolism. Many IDO1 inhibitors with different chemotypes have been developed, mainly targeted for use in anti-cancer immunotherapy. Lead optimization of direct heme iron-binding inhibitors has proven difficult due to the remarkable selectivity and sensitivity of the heme-ligand interactions. Here, we present experimental data for a set of closely related small azole compounds with more than 4 orders of magnitude differences in their inhibitory activities, ranging from millimolar to nanomolar levels. We investigate and rationalize their activities based on structural data, molecular dynamics simulations, and density functional theory calculations. Our results not only expand the presently known four confirmed chemotypes of sub-micromolar heme binding IDO1 inhibitors by two additional scaffolds but also provide a model to predict the activities of novel scaffolds.

Molecular conformations of aminophenylimidazoles exhibiting antiulcer activities

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