7412-05-7

Basic information

• Product Name: N-(1H-benzo[d]imidazol-2-yl)benzamide
• Synonyms: N-(1H-benzo[d]imidazol-2-yl)benzamide
• CAS NO: 7412-05-7
• Molecular Weight: 237.261
• Mol File: 7412-05-7.mol

Chemical Properties

• CAS DataBase Reference: N-(1H-benzo[d]imidazol-2-yl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1H-benzo[d]imidazol-2-yl)benzamide(7412-05-7)
• EPA Substance Registry System: N-(1H-benzo[d]imidazol-2-yl)benzamide(7412-05-7)

Safety Data

• Hazardous Substances Data: 7412-05-7(Hazardous Substances Data)

Upstream product

• 39145-59-0 o-phenylenediamine hydrochloride 
• 6074-65-3 benzoyl-dithiocarbonimidic acid diethyl ester 
• 58599-06-7 N,5-diphenyl-1,2,4-oxadiazol-3-amine 
• 24786-18-3 dimethyl N-benzoyldithiocarbonimidate 
• 95-54-5 1,2-diamino-benzene 
• 934-32-7 1H-benzimidazol-2-amine 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 162976-69-4 1H-benzimidazol-2-ylcarbamic acid methyl ester 
• 1006863-65-5 N-(2-iodophenyl)-N'-benzoylthiourea 
• 93-58-3 benzoic acid methyl ester 
• 532-55-8 Benzoyl isothiocyanate 

Downstream Products

• 125605-13-2 1-benzoyl-1,2,3,4,5,6-hexahydro-4-phenyl<1,3,6>triazocino<1,2-a>benzimidazole 
• 120625-27-6 1-(2-benzimidazolyl)-5-phenyl-1H-tetrazole 
• 65-85-0 benzoic acid 
• 19777-06-1 N-(1-methyl-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide 
• 19363-75-8 N-(1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide 
• 289908-97-0 bis(methanol)-bis[N-(benzoxazol-2-yl)-benzamidato]nickel(II) 
• 125605-29-0 1,2,3,4,5,6-hexahydro-4-phenyl<1,3,6>triazocino<1,2-a>benzimidazole 
• 138490-71-8 N-[4-(5,6,9,10-Tetrahydro-8H-4b,7,10,11-tetraaza-cycloocta[a]indene-7-sulfonyl)-phenyl]-methanesulfonamide 

Relevant articles and documents

Synthesis and fungicidal activity of 2-benzoylaminobenzimidazole complex compounds with copper

Special features of the formation of 2-benzoylaminobenzimidazole complexes with copper(II) chloride, sulfate, and acetate were studied. Optimal conditions of obtaining the complexes were found, and chemical compositions, some physicochemical properties, a

Synthesis, Fungicidal Activity, and Molecular Docking of 2-Acylamino and 2-Thioacylamino Derivatives of 1 H-benzo[ d]imidazoles as Anti-Tubulin Agents

This work deals with the synthesis and evaluation of fungicidal activity of benzimidazole derivatives, which are structural analogues of commercial anti-tubulin fungicides. A number of N-acyl and N-thioacyl derivatives of 2-amino-1H-benzo[d]imidazole were prepared, and their fungicidal activity against 13 strains of phytopathogenic fungi was studied. The most active compounds against the majority of the studied strains were 3a, 4l, and 4o, and the EC50 values of these compounds were in the range 2.5-20 μg/mL. Compound 3a showed the highest activity against the P. infestans strain, the growth of which is not suppressed by carbendazim. The formation of ligand-receptor complexes of various tautomeric forms of the studied benzimidazoles with homologous models of β-tubulins of B. cinerea, F. oxysporum, and P. infestans was modeled. Induced fit docking has been used for the simulation. The obtained data suggest the possibility of binding of benzimidazole fungicides to β-tubulin in the nocodazole cavity in the tautomeric form bearing a double exocyclic C=N bond. The importance of the formation of hydrogen bonds of benzimidazoles with the amino acid residue Val236 along with the Glu198 residue is also revealed in the present study.

Alternative and efficient method for the preparation of 2-acetamidobenzimidazoles

An alternative method for the synthesis of acetamidobenzimidazoles (3-6) has been developed, including the reacylation of methylbenzimidazol-2-ylcarbamate (carbendazim, MBC, 1) under the action of aliphatic and aromatic carboxylic acids. It was shown that with an increase in the size of the alkyl group and the reaction temperature (in the case of butyric acid), due to the decomposition of the resulting product, the yield of the target acyl products sharply decreases. The obtained compounds are homologues of the anthelmintic drug - N-(1H-benzimidazol-2-yl) acetamide (2-acetylaminobenzimidazole, 3). A possible mechanism of reacylation is presented.

2-Aminobenzimidazole and -benzoxazole as N-nucleophile in palladium-catalysed aminocarbonylation

Palladium-catalysed aminocarbonylation of aryl iodides in the presence of 2-aminobenzimidazole and 2-aminobenzoxazole as N-nucleophile was carried out. Single CO insertion took place, however, instead of the expected carboxamides (C(O)NH) the correspondin

Copper promoted C-S and C-N cross-coupling Reactions:The synthesis of 2-(N-Aryolamino)benzothiazoles and 2-(N-Aryolamino)benzimidazoles

The synthesis of 2-(N-aryolamino)benzothiazoles and 2-(N-aryolamino)benzimidazoles has been accomplished in the presence of copper catalyst. These reactions involve C-S and C-N cross-coupling reaction. All electron donating and withdrawing substituent's readily underwent the reaction to give target products in good to excellent yield. In addition, the reaction also gave target product in high yield with bulk scale.

Practical preparation of challenging amides from non-nucleophilic amines and esters under flow conditions

A fast and efficient protocol for the formation of amides from low nucleophilic amines and esters in flow is described. Products were obtained in good to excellent yields and with the advantage of simultaneous mixing of all reagents at once, avoiding steps for intermediate formation. The protocol is also suitable to be combined with ester synthesis, resulting in the preparation of amides in-line from haloarenes. This journal is

PTSA catalyzed straightforward protocol for the synthesis of 2-(N-acyl)aminobenzimidazoles and 2-(N-acyl)aminobenzothiazoles in PEG

An efficient PTSA catalyzed synthesis of 2-(N-acyl)aminobenzimidazoles and 2-(N-acyl)aminobenzothiazoles has been described using S-ethylated-N- acylthioureas as substrates and polyethylene glycol as solvent.

Phosphonium-mediated cyclization of N-(2-aminophenyl)thioureas: Efficient synthesis of 2-aminobenzimidazoles

BOP efficiently promoted the phosphonium-mediated cyclization of thioureas, leading to a convenient synthesis of 2-aminobenzimidazoles. Compared to conventional methods, the reactions were complete at room temperature with times ranging from a few minutes

Discovery and initial SAR of inhibitors of interleukin-1 receptor-associated kinase-4

High-throughput screening of a small-molecule compound library resulted in the identification of a novel series of N-acyl 2-aminobenzimidazoles that are potent inhibitors of interleukin-1 receptor-associated kinase-4.

A one-pot method for the synthesis of 2-aminobenzimidazoles and related heterocycles

A rapid and efficient one-pot method for the synthesis of 2-aminobenzimidazoles and related heterocycles is described. The reaction is mediated by a polymer-supported carbodiimide, which simplifies product isolation. The scope and limitations of this method are described.