1043906-11-1

Basic information

• Product Name: 1-(4-bromophenyl)-3-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one
• Synonyms: 1-(4-bromophenyl)-3-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one
• CAS NO: 1043906-11-1
• Molecular Weight: 303.158
• Mol File: 1043906-11-1.mol

Chemical Properties

• CAS DataBase Reference: 1-(4-bromophenyl)-3-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-bromophenyl)-3-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one(1043906-11-1)
• EPA Substance Registry System: 1-(4-bromophenyl)-3-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one(1043906-11-1)

Safety Data

• Hazardous Substances Data: 1043906-11-1(Hazardous Substances Data)

Upstream product

• 106-37-6 1.4-dibromobenzene 
• 4559-87-9 1-methyl-1-phenylurea 
• 3422-01-3 tert-butyl phenylcarbamate 
• 28131-24-0 tert-butyl N-methyl-N-(phenyl)carbamate 
• 2493-02-9 4-bromophenyl isocyanate 
• 100-61-8 N-methylaniline 
• 62-53-3 aniline 
• 77585-87-6 3-(4-bromophenyl)-1-methyl-1-phenylurea 
• 1849-01-0 1-methyl-2-benzimidazolone 
• 589-87-7 1,4-bromoiodobenzene 

Relevant articles and documents

I2-Mediated transition-metal-free aromatic C-H amination for the synthesis of benzimidazol-2-ones and related heterocycles

A practical iodine-mediated direct aromatic C-H amination reaction has been established for benzimidazol-2-one synthesis under transition-metal-free conditions. The required 1,3-diarylurea substrates are readily accessible by the addition of N-substituted arylamines to the corresponding isocyanates. This versatile and operationally simple synthetic process is broadly applicable to a wide range of 1,3-diarylureas and provides facile access to benzimidazol-2-ones and related heterocycles. Moreover, the present C-H amination reaction can also be performed directly from disubstituted amines and isocyanates without the purification of the urea intermediates in a scalable fashion.

Synthesis method for imidazolone compound

The invention relates to a synthesis method for an imidazolone compound shown in the formula (III). The synthesis method includes the steps that a compound of the formula (I) is reacted with a compound of the formula (II) in an organic solvent when a catalyst, an oxidizing agent, alkali and an assistant exist, aftertreatment is carried out after the reaction, and therefore the compound in formula (III) (please see the specification) is obtained, wherein R1 is selected from H or C1-C6 alkyl; R2 is selected from C1-C6 alkyl; R3 is selected from H or C1-C6 alkyl or halogen; X is halogen. According to the synthesis method, specific reaction substrates and the unique reaction system are adopted, the imidazolone compound is efficiently converted under the synthetic action of multiple reagent combinations accordingly, the high-yield technical effect is obtained, and quite-broad market prospects are achieved.

Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates

A simple and facile one-pot reaction has been developed to afford a diverse range of N,N′-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C-H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C-N bonds. A mechanism involving radical intermediates generated by single-electron transfer (SET) in the presence of a Ag2CO3 oxidant and Pd(OAc)2 Lewis acid is proposed. This protocol offers an operationally easy, simple, and robust approach with the use of readily available starting materials, good functional group tolerance, and high efficiency.

Metal-Free Oxidative C-H Amidation of N,N′-Diarylureas with PhI(OAc)2: Synthesis of Benzimidazol-2-one Derivatives

Benzimidazol-2-ones have various biological functions and are usually prepared by reactions of substituted benzene-1,2-diamines with carbonyl-containing compounds or intramolecular N-arylations using substrates with carbon-halogen bonds. However, the star

Sequential metal-catalyzed N-heteroarylation and C-C cross-coupling reactions: An expedient route to tris(hetero)aryl systems

This paper describes copper-catalyzed N-C heteroarylation of benzimidazole, 1-methylbenzimidazolone, imidazole and pyrrole. The products of these reactions then undergo palladium-catalyzed C-C cross-couplings with aryl or heteroarylboronic acids under Suzuki-Miyaura conditions to provide a rapid entry, from readily-available reagents, into tris(hetero)-aryl scaffolds comprising two or three N-heterocyclic rings. The sequential N-C and C-C couplings can be performed in a one-pot process (two examples are given: >50% overall yields). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.