2818-69-1

Usage

Chemical Properties

light brown powder

General Description

Light brown solid or fluffy powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Fire Hazard

Flash point data for 5-Chloro-2-methylbenzimidazole are not available; however, 5-Chloro-2-methylbenzimidazole is probably combustible.

InChI:InChI=1/C8H7ClN2/c1-5-10-7-3-2-6(9)4-8(7)11-5/h2-4H,1H3,(H,10,11)

Upstream product

• 86569-36-0 N,N'-diacetyl 4-chloro-1,2-phenylenediamine 
• 108-24-7 acetic anhydride 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 64-19-7 acetic acid 
• 51223-59-7 N-(2-amino-4-chlorophenyl)acetamide 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 39214-83-0 3-(4-nitrophenyl)isoxazol-5(4H)-one 
• 25755-82-2 3-(4-methylphenyl)isoxazol-5(4H)-one 
• 25755-85-5 3-(4-chlorophenyl)isoxazol-5-(4H)-one 
• 123-54-6 acetylacetone 
• 31709-47-4 3-(4-methoxyphenyl)isoxazol-5(4H)-one 
• 141-97-9 ethyl acetoacetate 
• 70254-61-4 4-hydroxy-6-methyl-2H-pyran-2-one 
• 78-39-7 Triethyl orthoacetate 

Downstream Products

• 46884-05-3 1-benzyl-5-chloro-2-methyl-1H-benzoimidazole 
• 46882-99-9 1-benzyl-6-chloro-2-methyl-1H-benzo[d]imidazole 
• 95864-47-4 5-chloro-N-<(2,4-dinitrophenyl)thio>-2-methylbenzimidazole 
• 95864-48-5 6-chloro-N-<(2,4-dinitrophenyl)thio>-2-methylbenzimidazole 
• 14537-47-4 6-Chlor-1,2-dimethyl-benzimidazol 
• 26960-04-3 5-chloro-1,2-dimethyl-1H-benzimidazole 
• 219318-65-7 2-(4-methylstyryl)-5-chlorobenzimidazole 
• 219318-56-6 2-(4-chlorostyryl)-5-chlorobenzimidazole 
• 219318-62-4 2-(4-nitrostyryl)-5-chlorobenzimidazole 
• 97338-89-1 2-styryl-5-chlorobenzimidazole 
• 54626-00-5 2-(4-methoxystyryl)-5-chlorobenzimidazole 
• 500865-96-3 5-chloro-2-methyl-1H-benzimidazol-6-amine 

Relevant academic research and scientific papers

Visible light initiated oxidative coupling of alcohols ando-phenylenediamines to synthesize benzimidazoles over MIL-101(Fe) promoted by plasmonic Au

The use of visible light to initiate one-pot synergistic/cascade reactions is a green and energy saving strategy. In this manuscript, we report that MIL-101(Fe) can act as a multifunctional catalyst to realize the oxidative condensation betweeno-phenylenediamines and alcohols to synthesize benzimidazoles under visible light. The deposition of plasmonic Au nanoparticles (Au NPs) on MIL-101(Fe) led to significantly improved activity. Both controlled experiments and electron spin resonance (ESR) results revealed that the production of benzimidazoles fromo-phenylenediamines and alcohols involves three sequential steps,i.e., the oxidative dehydrogenation of alcohols to produce aldehydes, the condensation betweeno-phenylenediamines and the aldehydes to produce Schiff bases and their oxidation to form benzimidazoles,viaa superoxide radical (O2˙?)-mediated pathway. The promoting effect of plasmonic Au NPs in this reaction can be ascribed to the effective transfer of the surface plasmon resonance (SPR)-excited hot electrons to the lowest unoccupied molecular orbital (LUMO) of MIL-101(Fe), which led to the generation of more active O2˙?radicals. This study not only provides a green and sustainable way for the synthesis of benzimidazoles, but also highlights the great potential of using rationally designed plasmonic metal NP/MOF nanocomposites as multifunctional catalysts for light initiated one-pot tandem/cascade reactions.

Rhodium catalyzed 2-alkyl-benzimidazoles synthesis from benzene-1,2-diamines and tertiary alkylamines as alkylating agents

Substituted 2-alkyl-benzimidazoles were synthesized from benzene-1,2-diamine and tertiary amines as alkylating agent under polystyrene supported rhodium (Rh@PS) nanoparticles (NPs) catalyzed conditions. The heterogeneous rhodium catalyst was applied first time for the synthesis of 2-alkyl-benzimidazoles. The reaction followed through oxidation of alkylamines, transamination, and oxidative cyclisation with benzene-1,2-diamines for the corresponding products synthesis with good yields. The process is applicable for vast substrate scope, several functional groups are tolerable, and the Rh@PS catalyst is recyclable up to four cycles without significant loss in catalytic activity.

Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus

The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.

Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid

Metal-free catalyzed intermolecular tandem Michael addition/cyclization has been developed for the synthesis of benzo[4,5]imidazo[1,2-a]pyridines from α-bromocinnamaldehyde and 2-substituted benzimidazoles. The reaction promoted by a simple inorganic base displays moderate to good yields and good functional group tolerance. The optical properties of some typical products have been investigated. We found that, due to the presence of the benzene ring at the C1-position of benzo[4,5]imidazo[1,2-a]pyridines which restricts intramolecular motion, as a new type of aggregation-induced emission (AIE) luminogen (AIEgen), they show very good solid-state fluorescence with quantum yields up to 88.80%. Importantly, the AIE performance of compound3bcan be useful to detect the nitroaromatic explosive picric acid (PA) with a detection limit and quenching constant of 42.5 nM and 7.27 × 104M?M, respectively.

Sustainable photocatalytic synthesis of benzimidazoles

Among the 17 Sustainable Development Goals presented by the United Nations in 2015, great attention is devoted to the production of goods and chemicals by use of renewable raw materials, by recycling of products and by extensive use of renewable energy sources. In this context, photocatalysis attracted great attention for the possibility to exploit Solar light to promote the desired chemical reactions. Besides its use in degradation of pollutants and in the production of fuels, some efforts have been devoted in the development of photocatalytic processes for the synthesis of fine chemicals with high added-value. In this work, we investigated the sustainable photocatalytic synthesis of benzimidazole derivatives through a one-pot, tandem process starting from a nitro compound and ethanol. By a photocatalytic approach, ethanol is dehydrogenated producing the hydrogen required for reduction of nitro groups and the aldehyde required for cyclization and production of the benzimidazole unit. Co-doping of TiO2 with B and N is beneficial to increase the photocatalytic activity in H2 production from ethanol. The effect of various metal co-catalysts (Pt, Pd Ag, Cu) have been evaluated on H2 production rate and on selectivity in the synthesis of substituted benzimidazoles: Pt showed the highest selectivity in the desired products while Pd demonstrated a great activity for hydrodehalogenation, with potential interest for degradation of persistent pollutants.

Benzimidazoles and benzothiazoles from styrenes and N-vinylimidazole via palladium catalysed oxidative C[dbnd]C and C[sbnd]N bond cleavage

Herein we report a first, palladium catalyzed, one-pot methodology for the synthesis of pharmacologically important benzimidazoles and benzothiazoles from readily available terminal aromatic olefins. The process involves sequential C[dbnd]C/C[sbnd]N bond cleavage followed by C[sbnd]N/C[sbnd]S bond formation.

A benzimidazole and synthetic method of derivative thereof (by machine translation)

The present invention provides a benzimidazole and its derivative synthesis method, the method through the imidazole chloride catalyzed O-phenylenediamine cyclized, realizes the multi-functional chain dibasic and imidazole and 2 - substituted benzimidazole synthesis, method is simple and economic, and the practicability is strong. This invention does not have any other catalyst or additive, synthetic method has good functional group tolerance and excellent yield and purity, reaction time is short, and does not need the harsh reaction conditions, is suitable for industrial production. (by machine translation)

Site-Selective C–H Functionalization of (Hetero)Arenes via Transient, Non-symmetric Iodanes

Fosu, Hambira, and colleagues describe the direct C–H functionalization of medicinally relevant arenes or heteroarenes. This strategy is enabled by transient generation of reactive, non-symmetric iodanes from anions and PhI(OAc)2. The site-selective incorporation of Cl, Br, OMs, OTs, and OTf to complex molecules, including within medicines and natural products, can be conducted by the operationally simple procedure included herein. A computational model for predicting site selectivity is also included. The discovery of new medicines is a time- and labor-intensive process that frequently requires over a decade to complete. A major bottleneck is the synthesis of drug candidates, wherein each complex molecule must be prepared individually via a multi-step synthesis, frequently requiring a week of effort per molecule for thousands of candidates. As an alternate strategy, direct, post-synthetic functionalization of a lead candidate could enable this diversification in a single operation. In this article, we describe a new method for direct manipulation of drug-like molecules by incorporation of motifs with either known pharmaceutical value (halides) or that permit subsequent conversion (pseudo-halides) to medicinally relevant analogs. This user-friendly strategy is enabled by combining commercial iodine reagents with salts and acids. We expect this simple method for selective, post-synthetic incorporation of molecular diversity will streamline the discovery of new medicines. A strategy for C–H functionalization of arenes and heteroarenes has been developed to allow site-selective incorporation of various anions, including Cl, Br, OMs, OTs, and OTf. This approach is enabled by in situ generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc)2. The utility of this mechanism is demonstrated via para-selective chlorination of medicinally relevant arenes, as well as site-selective C–H chlorination of heteroarenes. Spectroscopic, computational, and competition experiments describe the unique nature, reactivity, and selectivity of these transient, unsymmetrical iodanes.

Supported Rhodium (Rh@PS) Catalyzed Benzimidazoles Synthesis Using Ethanol/Methanol as C2H3/CH Source

An effective and stable polystyrene supported rhodium (Rh@PS) nano-catalyst has been synthesized by following reduction-deposition approach and applied for the selective benzimidazoles synthesis from 1,2-phenylenediamines and ethanol/methanol as C2H3/CH source. The ethanol/methanol in the presence of trace amounts of aerobic oxygen under Rh@PS catalysed condition, first participated in oxidation of alcohol followed by consecutive condensation, cyclization and hydrogen elimination reactions with 1,2-phenylenediamine gave the desired products in good yields. The Rh@PS catalyst in a single system performed both oxidation and reduction reactions in a selective/specific manner and applied for large substrate scope. Easy recovery, handling, stability, recyclability of the catalyst and less chance of metal contamination with the products are the added advantages of the process. (Figure presented.).

Imidazolium chloride-catalyzed synthesis of benzimidazoles and 2-substituted benzimidazoles from o-phenylenediamines and DMF derivatives

A facile, general, and economical synthesis of diversely functionalized benzimidazoles and 2-substituted benzimidazoles has been realized via the imidazolium chloride-catalyzed cyclization of o-phenylenediamines with DMF derivatives. This protocol shows a broad substrate scope for aliphatic, aromatic, and heteroaromatic amides. A series of benzimidazoles and 2-substituted benzimidazoles have been obtained in moderate to excellent yields.