233-53-4

Basic information

• Product Name: 1H-NAPHTH[1,2-D]IMIDAZOLE
• Synonyms: 1H-NAPHTH[1,2-D]IMIDAZOLE;1H-Naphth[1,2-d]imidazole(7CI,8CI,9CI);3H-benzo[e]benzimidazole
• CAS NO: 233-53-4
• Molecular Formula: C₁₁H₈N₂
• Molecular Weight: 168.19462
• Product Categories: BENZIMIDAZOLE
• Mol File: 233-53-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 174 °C(Solv: water (7732-18-5))
• Boiling Point: 463.1 °C at 760 mmHg
• Flash Point: 275.4 °C
• Appearance: /
• Density: 1.301 g/cm³
• Vapor Pressure: 2.59E-08mmHg at 25°C
• Refractive Index: 1.784
• PKA: 12.80±0.10(Predicted)
• CAS DataBase Reference: 1H-NAPHTH[1,2-D]IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-NAPHTH[1,2-D]IMIDAZOLE(233-53-4)
• EPA Substance Registry System: 1H-NAPHTH[1,2-D]IMIDAZOLE(233-53-4)

Safety Data

• Hazardous Substances Data: 233-53-4(Hazardous Substances Data)

Usage

General Description

1H-Naphth[1,2-d]imidazole, also known as imidazonaphthalene, is a heterocyclic aromatic compound with a fused ring structure. It belongs to the imidazole family of organic compounds and is structurally related to naphthalene. This chemical is used in the synthesis of pharmaceuticals, dyes, and agrochemicals. It has been studied for its potential applications in the field of medicinal chemistry, particularly as a building block for designing new drugs. Additionally, 1H-Naphth[1,2-d]imidazole has shown antimicrobial and antiviral activity in some studies, making it a potentially valuable compound for the development of new antimicrobial agents. However, further research is needed to fully understand its potential applications and mechanisms of action.

InChI:InChI=1/C11H8N2/c1-2-4-9-8(3-1)5-6-10-11(9)13-7-12-10/h1-7H,(H,12,13)

Upstream product

• 64-18-6 formic acid 
• 938-25-0 1,2-diaminonaphthalene 
• 73692-58-7 1,2-diaminonaphthalene dihydrochloride 
• 753401-37-5 5-styryl-1H-imidazole 

Downstream Products

• 108876-12-6 1-vinyl-1H-naphth[1,2-d]imidazole 
• 116866-62-7 6,7,8,9-Tetrahydronaphtho-(1,2)-imidazol 
• 82424-45-1 3-(4-nitrophenyl)naphtho<1,2-d>imidazole 
• 82424-44-0 1-(4-nitrophenyl)naphtho<1,2-d>imidazole 
• 82424-47-3 3-(2,4-dinitrophenyl)naphtho<1,2-d>imidazole 
• 82424-46-2 1-(2,4-dinitrophenyl)naphtho<1,2-d>imidazole 

Relevant articles and documents

Accelerated microdroplet synthesis of benzimidazoles by nucleophilic addition to protonated carboxylic acids

We report a metal-free novel route for the accelerated synthesis of benzimidazole and its derivatives in the ambient atmosphere. The synthetic procedure involves 1,2-aromatic diamines and alkyl or aryl carboxylic acids reacting in electrostatically charged microdroplets generated using a nano-electrospray (nESI) ion source. The reactions are accelerated by orders of magnitude in comparison to the bulk. No other acid, base or catalyst is used. Online analysis of the microdroplet accelerated reaction products is performed by mass spectrometry. We provide evidence for an acid catalyzed reaction mechanism based on identification of the intermediate arylamides. Their dehydration to give benzimidazoles occurs in a subsequent thermally enhanced step. It is suggested that the extraordinary acidity at the droplet surface allows the carboxylic acid to function as a C-centered electrophile. Comparisons of this methodology with data from thin film and bulk synthesis lead to the proposal of three key steps in the reaction: (i) formation of an unusual reagent (protonated carboxylic acid) because of the extraordinary conditions at the droplet interface, (ii) accelerated bimolecular reaction because of limited solvation at the interface and (iii) thermally assisted elimination of water. Eleven examples are shown as evidence of the scope of this chemistry. The accelerated synthesis has been scaled-up to establish the substituent-dependence and to isolate products for NMR characterization.

Synthesis and Photocylization of some 4-(5)Arylethenylimidazoles

The synthesis of eleven 4-(5)arylethenylimidazoles and their separation into cis and trans isomers is described.Ir, uv, nmr, and mass spectrometric data of the compounds are given.The photocyclization of the unsubstituted and p-substituted compounds is reported.