34734-23-1

Basic information

• Product Name: 1H-Benzimidazole, 1-(2-methylphenyl)-
• CAS NO: 34734-23-1
• Molecular Formula: C14H12N2
• Molecular Weight: 208.263
• Mol File: 34734-23-1.mol

Chemical Properties

• CAS DataBase Reference: 1H-Benzimidazole, 1-(2-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole, 1-(2-methylphenyl)-(34734-23-1)
• EPA Substance Registry System: 1H-Benzimidazole, 1-(2-methylphenyl)-(34734-23-1)

Safety Data

• Hazardous Substances Data: 34734-23-1(Hazardous Substances Data)

Upstream product

• 64-18-6 formic acid 
• 51-17-2 benzoimidazole 
• 16419-60-6 2-Methylphenylboronic acid 
• 615-37-2 ortho-methylphenyl iodide 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 73774-44-4 bis(2-methylphenyl)borinic acid 
• 636-98-6 p-nitrobenzene iodide 
• 95-52-3 2-Fluorotoluene 
• 95-46-5 2-methylphenyl bromide 

Relevant articles and documents

A Chemoselective and Desulfurative Chan–Lam Coupling: C–N Bond Formation between Benzimidazoline-2-Thiones and Arylboronic Acids

An efficient method for the chemoselective and desulfurative Chan–Lam cross-coupling based on benzimidazoline-2-thiones was developed. By modulating the amount of the catalyst Cu(OAc)2·H2O, alkali, temperature, and solvent, the desulfurizational C–N bond formation product (N-arylbenzimidazoles) could be selectively furnished smoothly. The features of this protocol are an inexpensive and readily available catalyst, ligand-free conditions, wide substrate scope, easy performance, and moderate to excellent yields. It shows potential synthetic value for the preparation of a diversity of arylbenzoheterocyclic compounds, which are potentially active in pharmaceuticals and agrochemicals.

Chan-Lam cross-coupling reaction based on the Cu2S/TMEDA system

A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted C–N bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported.

N, O-Bidentate ligand-tunable copper(II) complexes as a catalyst for Chan-Lam coupling reactions of arylboronic acids with 1 H-imidazole derivatives

An efficient procedure for Chan-Lam coupling reactions of arylboronic acids with 1H-imidazole derivatives using N,O-bidentate ligand-tunable copper(ii) complexes as a catalyst under base-free conditions has been developed. This protocol features mild reac

Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids

N-Arylation of (benz)imidazoles and amines with diarylborinic acids as cost-effective aryl source has been efficiently effected via Cu(OAc)2-catalyzed Chan-Lam coupling in assistance of tetramethylethylenediamine (TMEDA) in methanol and pyridine (Py) in dichloromethane, respectively, in air at room temperature. The diarylborinic acids could be well accommodated by the Chan-Lam coupling oxidative conditions containing a proper combination of bases and solvents. The steric hindrance appeared to affect the copper-catalyzed N-arylation using the high-order arylboron reagent more significantly than the electronic factors, especially for low reactive anilines and aliphatic amines.

Copper complex-catalysed C-N coupling reaction of aryl iodides with nitrogen-containing heterocycles

An efficient method for the copper-catalysed arylation of nitrogen-containing heterocycles is reported using 3-(diphenylphosphino) propanoic acid as a ligand in combination of CuCl. The C-N coupling reactions afford various N-arylated products in good to excellent yields.

Catalyst-free N-arylation using unactivated fluorobenzenes

Caught in a 'SNAr'e: A one-step, high-yielding, catalyst-free method is described for N-arylation of azoles and indoles from unactivated monofluorobenzenes. This SNAr reaction tolerates a wide range of substituents and can also generate halogenated N-aryl products. The reaction can also be performed simultaneously with or subsequent to a copper- or palladium-catalyzed cross-coupling reaction in the same pot. Copyright

Copper(II) hydroxide complexes of N-heterocyclic carbenes and catalytic oxidative amination of arylboronic acids

Reactions of the imidazolium salts or their corresponding silver carbene complexes with copper powder afforded unusual copper(II) hydroxide complexes of N-heterocyclic carbenes: [Cu2(μ-OH)(L1)](PF6) 2 (2; L1 = 3,5-bis(N-picolylimidazolylidenylmethy1)pyrazolate), [Cu4(μ3-OH)2(L2)2](PF 6)4 (3; L2 = 3,5-bis(N-pyridylimidazolylidenylmethy1) pyrazolate), and [Cu4(μ3-OH)2(L3) 2](PF6)4 (4; L3 = 3,5-bis(N- pyrimidylimidazolylidenylmethy1)pyrazolate). The same reaction of 3,5-bis(N-thiophenylimidazoliumylmethy1)pyrazole yielded a dinuclear Cu(II)-NHC complex, [Cu2(L4)2] (PF6)2 (5; L4 = 3,5-bis(N-thiophenylimidazolylidenylmethy1)pyrazolate). The complexes have been fully characterized by X-ray diffraction analysis, elemental analysis, and IR and ESI-MS spectra. A catalytic study shows that complex 4 is highly active in the N-arylation reactions of imidazoles and aromatic amines with arylboronic acids in methanol at room temperature under base-free conditions.

Copper-catalyzed N-arylation of hindered substrates under mild conditions

A mild, efficient method utilizing a copper-diamine catalyst at room temperature is reported for the coupling of hindered imidazoles with unsubstituted, orthzo-substituted, and bis-ortho-substi-tuted boronic acids in good to excellent yields. Aryl halides

Copper-catalyzed N-arylation of imidazoles and benzimidazoles

(Chemical Equation Presented) 4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good to excellent yields. Heteroaryl halides were also coupled in moderate to good yields. We also present the results obtained from a series of coupling reactions, which directly compare the use of L1c with other recently reported ligands.

Benzotriazole: an excellent ligand for Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides

Benzotriazole (BtH) is an efficient ligand for the Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides. A combination of CuI/BtH was found to be an efficient and inexpensive catalyst system to carry out the N-arylation of imidazoles affording the corresponding products in good to excellent yields.