3652-93-5

Basic information

• Product Name: 2-(1,3-dimethyl-2,3-dihydro-1H-benzimidazol-2-yl)phenol
• Synonyms: 2-(1,3-dimethyl-2,3-dihydro-1H-benzimidazol-2-yl)phenol;2,3-dihydro-2-(2-hydroxyphenyl)-1,3-dimethyl-1H-benzimidazole
• CAS NO: 3652-93-5
• Molecular Formula: C₁₅H₁₆N₂O
• Molecular Weight: 240.30034
• Mol File: 3652-93-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 150 °C
• Boiling Point: 353.2±42.0 °C(Predicted)
• Appearance: /
• Density: 1.182±0.06 g/cm3(Predicted)
• PKA: 9.30±0.35(Predicted)
• CAS DataBase Reference: 2-(1,3-dimethyl-2,3-dihydro-1H-benzimidazol-2-yl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,3-dimethyl-2,3-dihydro-1H-benzimidazol-2-yl)phenol(3652-93-5)
• EPA Substance Registry System: 2-(1,3-dimethyl-2,3-dihydro-1H-benzimidazol-2-yl)phenol(3652-93-5)

Safety Data

• Hazardous Substances Data: 3652-93-5(Hazardous Substances Data)

Usage

Chemical classification

Benzimidazole derivative

Functional group

Phenolic group

Biological activities

Anti-tumor, anti-microbial, and anti-inflammatory properties

Potential applications

Drug development, fluorescent probe for detecting metal ions

Versatility

Applicable in medicine, biology, and materials science fields

Upstream product

• 90-02-8 salicylaldehyde 
• 3213-79-4 N,N'-dimethyl-1,2-phenylenediamine 
• 49633-28-5 1,2-bis-(p-methylphenylsulfonamido)-benzene 
• 29627-62-1 N,N’-dimethyl-N,N’-di(p-toluenesulfonyl)-o-phenylenediamine 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 3204-31-7 1,3-Dimethyl-2,3-dihydro-1H-benzoimidazole 
• 113036-44-5 1,3-dimethyl-2-(2-phenox-1-yl)benzimidazolium 
• 108-95-2 phenol 
• 100672-51-3 2-Hydroxy-N-methyl-N-(2-methylamino-phenyl)-benzamide 
• 3653-06-3 2-(2-hydroxyphenyl)-1,3-dimethylbenzimidazolium iodide 
• 4217-54-3 9,10-dihydro-10-methylacridine 

Relevant articles and documents

Aryl-substituted dimethylbenzimidazolines as effective reductants of photoinduced electron transfer reactions

Photoinduced electron transfer (PET) reactions promoted by 2-aryl substituted 1,3-dimethylbenzimidazolines (Ar-DMBIH) were investigated. Excited states of Ar-DMBIH, formed by irradiation using light above 360 nm, initiate PET reductions of various organic substrates, including transformations of epoxy ketones to aldols, free radical rearrangements such as the Dowd-Beckwith ring-expansion and 5-exo hexenyl cyclization, deprotection of N-sulfonyl-indols, and allylation of acyl formates. In these processes, Ar-DMBIH possessing 1-naphthyl, 2-naphthyl, 1-pyrenyl and 9-anthryl substituents formally act as two electron and one proton donors while the hydroxynaphthyl substituted derivative serves as a two electron and two proton donor. On the basis of the results of absorption spectroscopy studies, cyclic voltammetry and DFT calculation, a mechanistic sequence for these reduction reactions is proposed that involves initial photoexcitation of the aryl chromophore of the Ar-DMBIH followed by single electron transfer (SET) to the organic substrate to generate the radical cation of benzimidazoline and the radical anion of the substrate.

2-Hydroxyphenyl-1,3-dimethylbenzimidazolines. Formal two hydrogen atom-donors for photoinduced electron transfer reactions

Both 2-(2′-hydroxyphenyl)-1,3-dimethylbenzimidazoline and 2-(4′-hydroxyphenyl)-1,3-dimethylbenzimidazoline were found to act as formal two hydrogen atom-donors for photoinduced electron transfer reactions of epoxy ketones and other carbonyl compounds.

Synthesis and Autoxidation of 1,3-Dialkyl-2-arylbenzimidazolines

During the attempted studies of the elimination reactions of 1,3-dimethyl-(I, R = CH3)- and 1,3-diethyl-(I, R = C2H5)-2-arylbenzimidazolines, a novel rearrangement has been observed to take place resulting in substituted amides by autoxidative ring-opening.