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Usage

Uses

Used in Polymer Industry:
1-(2-Propenyl)-2-benzimidazolidinone is used as a flame retardant and smoke suppressant for polymers to improve their fire resistance without compromising their mechanical properties. Its application ensures that the polymers meet stringent safety standards while maintaining their structural integrity.
Used in Textile Industry:
In the textile industry, 1-(2-Propenyl)-2-benzimidazolidinone is utilized as a flame retardant to enhance the fire safety of fabrics and garments. It helps in reducing the flammability of textiles, thereby providing an additional layer of protection to consumers and meeting industry-specific fire safety requirements.
Used in Electronics Industry:
1-(2-Propenyl)-2-benzimidazolidinone is employed as a flame retardant in the electronics industry to safeguard electronic components and devices from fire hazards. Its incorporation into electronic materials ensures compliance with fire safety regulations and reduces the risk of fire-related accidents.
Used in Cancer Treatment Research:
1-(2-Propenyl)-2-benzimidazolidinone has been studied for its potential antitumor properties, showing promise in cancer treatment. It is used as a subject of research for its possible application in developing new therapeutic agents against various types of cancer.
Used in Antimicrobial Applications:
PBD has demonstrated antimicrobial properties, making it a candidate for use in infection control. It is utilized as a subject of study for its potential to be developed into antimicrobial agents, which could be applied in various industries, including healthcare and food safety, to prevent the spread of infections.

InChI:InChI=1/C10H10N2O/c1-2-7-12-9-6-4-3-5-8(9)11-10(12)13/h2-6H,1,7H2,(H,11,13)

Upstream product

• 5097-82-5 5-phenyl-1H-tetrazolone 
• 1048344-57-5 1-allyl-1-(2-bromophenyl)urea 
• 13347-27-8 N-(2-Nitrophenyl)-N-prop-2-enylamine 
• 88-74-4 2-nitro-aniline 
• 20885-80-7 o-(Allylamino)benzohydroxamsaeure 
• 28736-09-6 2-<(prop-2'-enyl)amino>benzamide 
• 1042308-45-1 C₁₀H₁₁IN₂O 
• 95-54-5 1,2-diamino-benzene 
• 52099-72-6 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one 
• 107-11-9 1-amino-2-propene 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 556-56-9 allyl iodid 
• 106-95-6 allyl bromide 
• 13444-10-5 1,4-Dihydro-1-phenyl-4-(2-propenyl)-5H-tetrazol-5-on 

Downstream Products

• 95926-75-3 (E)-1,3-Dihydro-1-(1-propenyl)-2H-benzimidazol-2-on 

Relevant academic research and scientific papers

Direct Synthesis of N-Monosubstituted Benzimidazol-2-ones via Ph 3P-I 2-Mediated Reaction of Hydroxamic Acids

A facile approach for the synthesis of benzimidazolones via a Ph3P-I2 promoted reaction of hydroxamic acids is reported. Upon Lossen-type rearrangement of the O-activated hydroxamic acids, the in situ generated isocyanates undergo an intramolecular attack by ortho N-nucleophiles producing the cyclized products in good yields under mild conditions. The method allows the direct preparation of a single regioisomer of N-monosubstituted derivatives using readily accessible starting materials and low-cost reagents with broad substrate scope.

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.

Highly efficient synthesis of ureas and carbamates from amides by iodosylbenzene-induced hofmann rearrangement

A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. Symmetric and asymmetric ureas and carbamates can be prepared by this procedure in up to 98 % yield. Ureidopeptides can also be prepared in good yield by this method. A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. By using this method, heterocyclic products can be easily obtained in excellent yield. Ureidopeptides can also be prepared in good yield by this procedure. Copyright

Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones

The copper-catalyzed intramolecular N-arylation of 2-bromoarylureas performed in water leading to the benzo[d]imidazolone framework is reported. The scope of the methodology presented herein proved to?be broad and afforded a significant number of benzoimidazolones in good to excellent yields. The reported protocol is based on the use of CuI and TMEDA acting both as the ligand and as the base in a water solution, which allows for the easy separation of the catalyst containing aqueous phase from the products by simple extraction. Additionally, the N- versus O-arylation competitive processes are also discussed.

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.

Cascade coupling/cyclization process to N-substituted 1,3- dihydrobenzimidazol-2-ones

Assembly of N-substituted 1,3-dihydrobenzimidazol-2-ones is achieved starting from methyl o-haloarylcarbamates via a Cul/amino acid catalyzed coupling with amines and subsequent condensative cyclization. A number of functional groups are tolerated by thes

2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxamides with selective affinity for the 5-HT4 receptor: Synthesis and structure-affinity and structure-activity relationships of a new series of partial agonist and antagonist derivatives

A series of 2,3-dihydro-2-oxo-1H-benzimidazole-l-carboxamide derivatives bearing a piperazine moiety was synthesized. Their in vitro 5-HT4, 5-HT3, and D2 receptors affinities were evaluated by radioligand binding assay. For selected compounds functional studies at the 5-HT4 receptor were made by using precontracted (by carbachol) preparations of rat esophageal tunica muscularis mucosae (TMM). The influence of the 3-substituent of the benzimidazole ring, the 4-substituent of the piperazine moiety, and the alkylene spacer was studied. Compounds with an ethyl or a cyclopropyl substituent in the 3-position of the benzimidazole ring showed moderate to high affinity (K(i) = 6.7-75.4 nM) for the 5-HT4 receptor with selectivity over 5-HT3 and D2 receptors and moderate antagonist activity (pK(b) = 6.19- 7.73). Compounds with an isopropyl substituent in the 3-benzimidazole position exhibited moderate and selective 5-HT4 affinity (K(i) ≥ 38.9 nM) and a partial agonist activity (5a, i.a. = 0.94) higher than that of the reference compound BIMU 8 (i.a. = 0.70). This reversal of the pharmacological activity due only to a small structural difference might confirm the existence of two binding sites on the 5-HT4 receptor. In the alkylene spacer, a two-methylene chain is favorable to optimize the affinity and the antagonist or the partial agonist activity. In the ethyl and cyclopropyl series, 5-HT4 antagonist activity seems to be unrelated to the size of the 4-substituent of the piperazine moiety, whereas a methyl group is optimal for high partial agonist activity in the isopropyl series; however, the presence of a butyl substituent is a favorable pattern for 5-HT4 antagonism and even causes a reversal of the pharmacological profile in the isopropyl series (5h, pK(b) = 7.94). N-Butyl quaternization of 5a led to an improvement in affinity for the 5-HT4 receptor and maintained the high partial agonist activity (5r, K(i) = 66.3 nM, i.a. = 0.93).

Regiospecific functionalization of 1,3-dihydro-2H-benzimidazol-2-one and structurally related cyclic urea derivatives

Methods for selectively protecting one of the degenerate nitrogen atoms of the cyclic urea derivatives 1,3-dihydro-2H-benzimidazol-2-one (6a), 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (11), 1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-ones (20), 1,3-dihydro-

Photoextrusion of Nitrogen from 1,4-Dihydro-1-phenyl-5H-tetrazol-5-ones and -thiones. Benzimidazolones and Carbodiimides

Alkylation of 1-phenyltetrazolone 10a with 2-cyclohexen-1-yl bromide followed by dehydrogenation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone permits introduction of a phenyl group at N-4 of the tetrazole ring via the sequence 10a -> 10f -> 10g.The photoextrusion of molecular nitrogen from the (N-4)-substituted 1-phenyltetrazolones, 10a (hydrogen), 10b (methyl), 10d,e (propenyl), and 10g (phenyl) produces essentially quantitative yields of the corresponding benzimidazolones 14a,b,d,e,g.On irradiation of the 1-phenyltetrazolethiones 8b,f,g the carbodiimides 22b,f,g are obtained together with molecular nitrogen and sulfur, while 8a affords phenylcyanamide (25).In contrast to the thermolysis, which is known to give 2-(methylamino)benzothiazole (21b), photolysis of the (phenylimino)-1,2,3,4-thiatriazole 24, an isomer of methylphenyltetrazolethione 8b, also yields molecular nitrogen, sulfur, and methylphenylcarbodiimide (22b).

Synthesis of 1-Alkyl and 1,3-Dialkyl-2-benzimidazolones from 1-Alkenyl-2-benzimidazolones using Phase-Transfer Catalysts Technique

A general synthetic route to 1-alkyl and 1,3-dialkyl-2-benzimidazolones from 1-alkenyl-2-benzimidazolenes using phase-transfer catalysis conditions is described.