875004-73-2

Basic information

• Product Name: 2H-Benzimidazol-2-one, 1,3-dihydro-1-(4-methylphenyl)-
• CAS NO: 875004-73-2
• Molecular Formula: C14H12N2O
• Molecular Weight: 224.262
• Mol File: 875004-73-2.mol

Chemical Properties

• CAS DataBase Reference: 2H-Benzimidazol-2-one, 1,3-dihydro-1-(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Benzimidazol-2-one, 1,3-dihydro-1-(4-methylphenyl)-(875004-73-2)
• EPA Substance Registry System: 2H-Benzimidazol-2-one, 1,3-dihydro-1-(4-methylphenyl)-(875004-73-2)

Safety Data

• Hazardous Substances Data: 875004-73-2(Hazardous Substances Data)

Upstream product

• 106-49-0 p-toluidine 
• 1493-27-2 ortho-nitrofluorobenzene 
• 52753-44-3 (2-nitrophenyl)-p-tolylamine 
• 5720-05-8 4-methylphenylboronic acid 
• 769968-23-2 N-((2-iodophenylimino)methylene)-4-methylbenzenamine 
• 873998-68-6 N-(2-bromo-phenyl)-N'-p-tolyl-urea 
• 710316-98-6 1-(2-iodophenyl)-3-p-tolylurea 
• 91806-09-6 N¹-(p-tolyl)benzene-1,2-diamine 
• 57-13-6 urea 

Downstream Products

• 875004-74-3 2-chloro-1-p-tolyl-1H-benzimidazole 

Relevant articles and documents

Efficient domino synthesis of benzimidazole derivatives: Copper catalysis versus transition metal-free conditions

An efficient and facile assembly of 2-substituted benzimidazoles and 2-benzimidazolones has been developed. Under very mild copper catalysis or transition metal-free conditions, a wide range of the 2-alkyl/alkenyl benzimidazole derivatives can be conveniently and selectively synthesized through the domino reactions of o-haloarylcarbodiimides with active methylene species. Interesting complimentary effect was discovered under the two different sets of conditions. Furthermore, a series of 1,3-disubstituted 2-benzimidazolones were facilely assembled from o-haloarylcarbodiimides and α,β-unsaturated esters.

Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source

A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.

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.

Discovery of novel, orally available benzimidazoles as melanin concentrating hormone receptor 1 (MCHR1) antagonists

Melanin concentrating hormone (MCH) is an important mediator of energy homeostasis and plays role in several disorders such as obesity, stress, depression and anxiety. The synthesis and biological evaluation of novel benzimidazole derivatives as MCHR1 antagonists are described. The in vivo proof of principle for weight loss with a lead compound from this series is exemplified.

Copper-catalyzed intramolecular cyclization to N-substituted 1,3-dihydrobenzimidazol-2-ones

(Chemical Equation Presented) An efficient and convenient method was developed for preparing N-substituted 1,3-dihydrobenzimidazol-2-ones from Na?2-substituted N-(2-halophenyl)ureas via a CuI/DBU-catalyzed cyclization in DMSO under microwave heating. High yields were obtained and a variety of functional groups were tolerated under these conditions, including Na?2-aryl, alkyl, heterocyclic, various N-(substituted 2-halophenyl) and N-(2-iodopyridyl)ureas. ? 2008 American Chemical Society.

MEDICINAL USE OF RECEPTOR LIGANDS

Compounds of formula (I) are ligands of the melanin concentrating hormone-1 receptor (MCH-1 R), useful in the treatment of diseases responsive to modulation of melanin concentrating hormone (MCH) activity, for example feeding disorders and diseases for which obesity is a risk factor (I): wherein ring B is selected from specific substituted phenyl or benz-fused 5-membered N-containing heterocycles defined in the specification; R, is attached to a ring carbon of ring B, and represents hydrogen, F, Cl, or -OCH3; X is =CH- or =N-; L, is -CH2- or -CH2CH2- ; L2 is a bond, -CH2- or -CO-; R2 is H or C,-C3 alkyl, or -N(R2) L,- is selected from specific cyclic amino linker radicals as defined in the specification; ring A is selected from specific N- containing heterocyclic rings as defined in the specification.