1-(4-nitrophenyl)-1H-benzimidazole

Base Information

• Chemical Name: 1-(4-nitrophenyl)-1H-benzimidazole
• CAS No.: 22492-14-4
• Molecular Formula: C13H9N3O2
• Molecular Weight: 239.233
• DSSTox Substance ID: DTXSID70401969
• Nikkaji Number: J2.211.894C
• Wikidata: Q82205300
• ChEMBL ID: CHEMBL345970
• Mol file: 22492-14-4.mol

Synonyms:22492-14-4;1-(4-nitrophenyl)-1H-benzimidazole;1-(4-nitrophenyl)-1H-1,3-benzodiazole;1-(4-Nitrophenyl)-1H-benzo[d]imidazole;1-(4-nitrophenyl)benzimidazole;1-Phenylbenzimidazole deriv. 45;SBB024797;1-(p-nitrophenyl)benzimidazole;BDBM3828;CHEMBL345970;SCHEMBL3834819;DTXSID70401969;MFCD03937392;STK120236;1-(4-Nitrophenyl)-1H-benzoimidazole;AKOS005167722;CF-0282;CS-0270442;EN300-231375

Chemical Property of 1-(4-nitrophenyl)-1H-benzimidazole

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 239.069476538
• Heavy Atom Count: 18
• Complexity: 310

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N=CN2C3=CC=C(C=C3)[N+](=O)[O-]

Technology Process of 1-(4-nitrophenyl)-1H-benzimidazole

There total 7 articles about 1-(4-nitrophenyl)-1H-benzimidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

benzoimidazole (51-17-2,79351-71-6) + para-nitrophenyl bromide (586-78-7) → 1-(4-nitrophenyl)-1H-benzimidazole (22492-14-4)

Guidance literature:

With copper(I) 2-hydroxy-3-methylbenzoate; potassium carbonate; In dimethyl sulfoxide; at 110 ℃; for 3h;

DOI:10.1016/j.tetlet.2014.03.117

Reference yield: 98.0%

benzoimidazole (51-17-2,79351-71-6) + 4-chlorobenzonitrile (100-00-5) → 1-(4-nitrophenyl)-1H-benzimidazole (22492-14-4)

Guidance literature:

With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride; at 140 - 145 ℃; for 24h;

DOI:10.1055/s-2008-1067014

Reference yield: 96.0%

benzoimidazole (51-17-2,79351-71-6) + 4-Fluoronitrobenzene (350-46-9,178603-76-4) → 1-(4-nitrophenyl)-1H-benzimidazole (22492-14-4)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; for 8h;

upstream raw materials:

benzoimidazole

4-Fluoronitrobenzene

4-chlorobenzonitrile

para-nitrophenyl bromide

Downstream raw materials:

Br^(1-)*C₂₅H₃₄N₃O₂⁽¹⁺⁾

3-nitro-5,6-diphenylbenzo[4,5]imidazo[1,2-a]quinoline

3-[2-{[(1S)-1-(hydroxymethyl)-2,2-dimethylpropyl]amino}-2-oxoethyl]-1-(4-nitrophenyl)-1H-benzimidazolium chloride

C₂₈H₂₁N₃O₃

Refernces

1-(4-Nitrophenyl)-benzimidazolium-based ratiometric chromogenic probes for cyanide ion

10.1016/j.tetlet.2009.05.047

The study presents the development of 1,3- and 1,4-bis-[1-(4-nitrophenyl)-benzimidazolium-3-methylene]benzene-based molecular probes that selectively interact with cyanide ions, causing a shift in absorbance from 270 nm to 376 nm. These probes are designed for the ratiometric chromogenic estimation of cyanide ions within the concentration range of 1–270 μM, which is crucial for practical applications due to cyanide's toxicity and environmental significance. The chemicals used in the study include 1-(4-nitrophenyl)benzimidazole, dodecylbromide, NH4PF6, and various anions such as AcO-, F-, CN-, and H2PO4-. These chemicals serve to synthesize the probes and test their selectivity and sensitivity towards cyanide ions. The probes were found to be highly selective and sensitive to cyanide ions, with the ability to estimate concentrations independent of the receptor concentration, making them valuable tools for detecting cyanide in environmental and biological samples.

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