2735-62-8

Basic information

• Product Name: (1-Methyl-1H-benzoimidazol-2-yl)acetonitrile
• Synonyms: 1H-Benzimidazole-2-acetonitrile,1-methyl-(9CI);(1-METHYL-1H-BENZIMIDAZOL-2-YL)ACETONITRILE;1-Methyl-1H-benzimidazole-2-acetonitrile;1-Methyl-2-(cyanomethyl)-1H-benzoimidazole;(1-Methyl-1H-benzoimidazol-2-yl)acetonitrile;2-(1-methylbenzimidazol-2-yl)acetonitrile;2-(1-methylbenzimidazol-2-yl)ethanenitrile;1-Methyl-2-benziMidazolylacetonitrile
• CAS NO: 2735-62-8
• Molecular Formula: C₁₀H₉N₃
• Molecular Weight: 171.2
• Product Categories: BENZIMIDAZOLE
• Mol File: 2735-62-8.mol

Chemical Properties

• Boiling Point: 380.4 °C at 760 mmHg
• Flash Point: 183.9 °C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 5.45E-06mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (1-Methyl-1H-benzoimidazol-2-yl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Methyl-1H-benzoimidazol-2-yl)acetonitrile(2735-62-8)
• EPA Substance Registry System: (1-Methyl-1H-benzoimidazol-2-yl)acetonitrile(2735-62-8)

Safety Data

• Hazardous Substances Data: 2735-62-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1-Methyl-1H-benzoimidazol-2-yl)acetonitrile is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure and properties make it a valuable component in the development of new drugs and medications.
Used in Agrochemical Industry:
In the agrochemical industry, (1-Methyl-1H-benzoimidazol-2-yl)acetonitrile is utilized as a precursor in the production of various agrochemicals. Its versatility in chemical reactions allows for the creation of compounds that can be used in crop protection and other agricultural applications.
Used in Organic Compounds Synthesis:
(1-Methyl-1H-benzoimidazol-2-yl)acetonitrile is also used as a building block in the synthesis of other organic compounds. Its reactivity and functional groups make it a suitable candidate for various organic reactions, leading to the formation of a wide range of products.
Safety Precautions:
When handling (1-Methyl-1H-benzoimidazol-2-yl)acetonitrile, it is important to take necessary safety precautions to avoid potential hazards. MCA can be hazardous if not handled properly, and it is crucial to avoid contact with skin, eyes, and inhalation of its vapors. Personal protective equipment, such as gloves, goggles, and masks, should be worn when working with MCA. Additionally, it is recommended to work in a well-ventilated area to minimize the risk of exposure to its vapors.

InChI:InChI=1/C10H9N3/c1-13-9-5-3-2-4-8(9)12-10(13)6-7-11/h2-5H,6H2,1H3

Upstream product

• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 105-34-0 methyl 2-cyanoacetate 
• 4414-88-4 1H-benzimidazol-2-acetonitrile 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 95-54-5 1,2-diamino-benzene 
• 372-09-8 cyanoacetic acid 
• 88-73-3 2-Chloronitrobenzene 
• 107-91-5 cyanoacetic acid amide 
• 612-28-2 2-nitro-N-methylaniline 

Downstream Products

• 146495-32-1 (1-Methylbenzimidazol-2-yl)(cyclohexylidenamino)acetamid 
• 135408-64-9 3-Amino-2-benzyl-4-(1-methyl-1H-benzoimidazol-2-yl)-7-nitro-2H-isoquinolin-1-one 
• 144459-21-2 4-(1-Methyl-1H-benzoimidazol-2-yl)-7-nitro-1,1-dioxo-2-phenyl-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazin-3-ylamine 
• 120340-91-2 2-Amino-1-benzyl-3-(1-methylbenzimidazol-2-yl)pyrrolo<2,3-b>quinoxaline 
• 144459-20-1 2-Benzyl-4-(1-methyl-1H-benzoimidazol-2-yl)-7-nitro-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazin-3-ylamine 
• 5114-84-1 (1,3-dimethyl-1,3-dihydro-2H-benzoimidazol-2-ylidene)acetonitrile 
• 67483-51-6 N-Methyl-2-(α-hydroxyimino-α-cyanomethyl)benzimidazole 
• 66094-30-2 2-benzyl-2-(1-methyl-1H-benzoimidazol-2-yl)-3-phenyl-propionitrile 
• 139399-42-1 α-(1-methyl-2-benzimidazolyl)-2,4-dihydroxy-5-ethylacetophenone 

Relevant articles and documents

N-substituted benzimidazole acrylonitriles as in vitro tubulin polymerization inhibitors: Synthesis, biological activity and computational analysis

We present the design, synthesis and biological activity of novel N-substituted benzimidazole based acrylonitriles as potential tubulin polymerization inhibitors. Their synthesis was achieved using classical linear organic and microwave assisted techniques, starting from aromatic aldehydes and N-substituted-2-cyanomethylbenzimidazoles. All newly prepared compounds were tested for their antiproliferative activity in vitro on eight human cancer cell lines and one reference non-cancerous assay. N,N-dimethylamino substituted acrylonitriles 30 and 41, bearing N-isobutyl and cyano substituents placed on the benzimidazole nuclei, showed strong and selective antiproliferative activity in the submicromolar range of inhibitory concentrations (IC50 0.2–0.6 μM), while being significantly less toxic than reference systems docetaxel and staurosporine, thus promoting them as lead compounds. Mechanism of action studies demonstrated that two most active compounds inhibited tubulin polymerization. Computational analysis confirmed the suitability of the employed benzimidazole-acrylonitrile skeleton for the binding within the colchicine binding site in tubulin, thus rationalizing the observed antitumor activities, and demonstrated that E-isomers are active substances. It also provided structural determinants affecting both the binding position and the matching affinities, identifying the attached NMe2 group as the most dominant in promoting the binding, which allows ligands to optimize favourable cation???π and hydrogen bonding interactions with Lys352.

Synthesis, computational analysis, and antiproliferative activity of novel benzimidazole acrylonitriles as tubulin polymerization inhibitors: Part 2

We used classical linear and microwave-assisted synthesis methods to prepare novel N-substituted, benzimidazole-derived acrylonitriles with antiproliferative activity against several cancer cells in vitro. The most potent systems showed pronounced activit

A reactive primary fluorescence switch-on sensor for Hg2+ and the generated fluorophore as secondary recognition receptor toward Cu2+ in aqueous acetonitrile solution

A new N-methylbenzoimidazole-based fluorescence “turn-on” chemodosimeter (VPBA) was synthesized and characterized for cation to cation relay recognition (CCRR) with high sequence specificity (Hg2+?→?Cu2+). The selectivity and sensiti

Design, synthesis and biological evaluation of 5-amino-4-(1H-benzoimidazol-2-yl)-phenyl-1,2-dihydro-pyrrol-3-ones as inhibitors of protein kinase FGFR1

Fibroblast growth factor receptor 1 (FGFR1) plays an important role in tumorigenesis and is therefore an attractive target for anticancer therapy. Using molecular docking approach we have identified inhibitor of FGFR1 belonging to 5-amino-4-(1H-benzoimidazol-2-yl)-phenyl-1,2-dihydro-pyrrol-3-ones with IC50 value of 3.5 μM. A series of derivatives of this chemical scaffold has been synthesized and evaluated for inhibition of FGFR1 kinase activity. It was revealed that the most promising compounds 5-amino-1-(3-hydroxy-phenyl)-4-(6-methyl-1H-benzoimidazol-2-yl)-1,2-dihydro-pyrrol-3-one and 5-amino-4-(1H-benzoimidazol-2-yl)-1-(3-hydroxy-phenyl)-1,2-dihydro-pyrrol-3-one inhibit FGFR1 with IC50 values of 0.63 and 0.32 μM, respectively, and posses antiproliferative activity against KG1 myeloma cell line with IC50 values of 5.6 and 9.3 μM. Structure-activity relationships have been studied and binding mode of this chemical class has been proposed.

Synthesis and Mechanism Studies of 1,3-Benzoazolyl Substituted Pyrrolo[2,3-b]pyrazine Derivatives as Nonintercalative Topoisomerase II Catalytic Inhibitors

Novel topoisomerase II (Topo II) inhibitors have gained considerable interest for the development of anticancer agents. In this study, a series of 1,3-benzoazolyl-substituted pyrrolo[2,3-b]pyrazine derivatives were designed, synthesized, and evaluated as potential Topo II catalytic inhibitors. It was found that some of derivatives had good antiproliferative activity on seven cancer cell lines, especially on HL-60/MX2, a cancer cell line derivative from HL-60 that is resistant to Topo II poison. Topo II mediated DNA relaxation assay results showed that derivatives could significantly inhibit the activity of Topo II, and the structure-activity relationship studies indicated the importance of the alkylamino side chain and the benzoazolyl group. Further mechanism studies revealed that derivatives function as Topo II nonintercalative catalytic inhibitors and may block the ATP binding site of Topo II. Moreover, flow cytometric analysis showed that this class of compounds could induce apoptosis of HL-60 cells.

Near-infrared-absorbing composition, cured film, near-infrared-absorbing filter, solid-state imaging element, and infrared sensor

Provided are a near-infrared-absorbing composition whereby it is possible to form a film having excellent visible transparency and near-infrared shielding properties, and a cured film, a near-infrared-absorbing filter, a solid-state imaging element, and an infrared sensor. A near-infrared-absorbing composition including a resin and a compound represented by general formula (1), the compound having a maximum absorption wavelength in a wavelength range of 750-830 nm in a film when a film is formed using the near-infrared-absorbing composition, and the value obtained by dividing the absorbance at a wavelength of 555 nm by the absorbance at the maximum absorption wavelength being 0.10 or less.

Development of benzimidazole derivatives to inhibit HIV-1 replication through protecting APOBEC3G protein

Human APOBEC3G (apolipoprotein B mRNA-editing enzyme, catalytic polypeptide-like 3G, A3G) is a potent restriction factor against human immunodeficiency virus type 1 (HIV-1) by inducing hypermutation of G to A in viral genome after its incorporation into virions. HIV-1 Vif (Virion Infectivity Factor) counteracts A3G by inducing ubiquitination and proteasomal degradation of A3G protein. Vif-A3G axis therefore is a promising therapeutic target of HIV-1. Here we report the screening, synthesis and SAR studies of benzimidazole derivatives as potent inhibitors against HIV-1 replication via protecting A3G protein. Based on the steep SAR of the benzimidazole scaffold, we identified compound 14 and 26 which provided the best potency, with IC50 values of 3.45 nM and 58.03 nM respectively in the anti-HIV-1 replication assay in H9 cells. Compound 14 and 26 also afforded protective effects on A3G protein level. Both compounds have been proved to be safe in acute toxicological studies. Taken together, we suggest that these two benzimidazole derivatives can be further developed as a new category of anti-HIV-1 leads.

Deorphaning pyrrolopyrazines as potent multi-target antimalarial agents

The discovery of pyrrolopyrazines as potent antimalarial agents is presented, with the most effective compounds exhibiting EC50 values in the low nanomolar range against asexual blood stages of Plasmodium falciparum in human red blood cells, and Plasmodium berghei liver schizonts, with negligible HepG2 cytotoxicity. Their potential mode of action is uncovered by predicting macromolecular targets through avant-garde computer modeling. The consensus prediction method suggested a functional resemblance between ligand binding sites in non-homologous target proteins, linking the observed parasite elimination to IspD, an enzyme from the non-mevalonate pathway of isoprenoid biosynthesis, and multi-kinase inhibition. Further computational analysis suggested essential P. falciparum kinases as likely targets of our lead compound. The results obtained validate our methodology for ligand- and structure-based target prediction, expand the bioinformatics toolbox for proteome mining, and provide unique access to deciphering polypharmacological effects of bioactive chemical agents. Pyrrolopyrazines show strong activity against Plasmodium falciparum parasites and Plasmodium berghei liver schizonts. In-depth bioinformatical analysis and target panel screening, suggesting IspD and multi-kinase inhibition, revealed their likely mode of action. The composite computational approach provides a unique access to deciphering polypharmacological effects of new bioactive chemical agents.

Unexpected regiospecific reduction of the double bond by NaBH4 in 2-(1-methyl/1H-benzimidazole-2-yl)-3-aryl-acrylonitrile

Condensation of (1H-benzimidazole-2-yl)-acetonitrile 1 with aromatic aldehydes in 5% NaOH solution gave the corresponding 2-(1H-benzimidazole-2-yl)- 3-aryl-acrylonitrile 2, which on treatment with NaBH4 in ethanol unexpectedly gave 2-(1H-benzimidazole-2-yl)-3-aryl-propionitrile 3 by the regiospecific reduction of the double bond. Shaking a solution of 2 with H2/Pd-C in methanol also gave 3. Reaction of 2 with DMS gave the corresponding N-methylated analogue 5, which also with NaBH4 gave 6, once again by the regiospecific reduction of the double bond as in the case of 1-demethylated analogue (i.e., 2). Copyright Taylor & Francis Group, LLC.