1849-02-1

Basic information

• Product Name: 1H-Benzimidazole,2-chloro-1-methyl-(9CI)
• Synonyms: 1H-Benzimidazole,2-chloro-1-methyl-(9CI);2-Chloro-1-methylbenzimidazole;2-Chloro-1-Methyl-1H-Benzimidazole;1H-BenziMidazole,2-chloro-1-Methyl;2-Chloro-1-Methyl-1,3-benzodiazole
• CAS NO: 1849-02-1
• Molecular Formula: C₈H₇ClN₂
• Molecular Weight: 166.61
• Product Categories: BENZIMIDAZOLE;API intermediates
• Mol File: 1849-02-1.mol

Chemical Properties

• Melting Point: 117-117.5 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 303.4°C at 760 mmHg
• Flash Point: 137.3°C
• Appearance: White to yellow/Solid
• Density: 1.3g/cm³
• Vapor Pressure: 0.000931mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3.86±0.10(Predicted)
• CAS DataBase Reference: 1H-Benzimidazole,2-chloro-1-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole,2-chloro-1-methyl-(9CI)(1849-02-1)
• EPA Substance Registry System: 1H-Benzimidazole,2-chloro-1-methyl-(9CI)(1849-02-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1849-02-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole,2-chloro-1-methyl-(9CI) is used as a building block for the synthesis of various pharmaceuticals. Its potent inhibitory effect on the enzyme poly(ADP-ribose) polymerase makes it a potential candidate for cancer treatment. It can be incorporated into drug molecules to target and inhibit this enzyme, thereby exhibiting anticancer properties.
Used in Agrochemical Industry:
1H-Benzimidazole,2-chloro-1-methyl-(9CI) is used in the development of insecticides and anthelmintic drugs. The benzimidazole derivatives, including 1H-Benzimidazole,2-chloro-1-methyl-(9CI), have shown activity against a wide range of pests and parasites. By incorporating 1H-Benzimidazole,2-chloro-1-methyl-(9CI) into agrochemical formulations, it can help control and eliminate harmful pests and parasites in agricultural settings, thereby protecting crops and livestock.

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

Upstream product

• 7022-37-9 1-methyl-2-hydrazinobenzimidazole 
• 616-47-7 1-methyl-1H-imidazole 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 95-54-5 1,2-diamino-benzene 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 75-18-3 dimethylsulfide 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 1849-01-0 1-methyl-2-benzimidazolone 
• 1632-83-3 1-Methylbenzimidazole 
• 109-72-8 n-butyllithium 
• 7732-18-5 water 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 

Downstream Products

• 78765-36-3 2-(4-Chloro-phenoxy)-1-methyl-1H-benzoimidazole 
• 1516-73-0 2-azido-1-methyl-1H-benzo[d]imidazole 
• 384843-95-2 5-bromo-2-hydroxyisophthalaldehyde bis[(1-methyl-1H-benzimidazol-2-yl)hydrazone] 
• 27097-08-1 N-benzyl-1-methyl-1H-benzo[d]imidazol-2-amine 
• 6595-21-7 1-methyl-2-methylaminobenzimidazole 
• 78765-43-2 1-Methyl-2-(4-octyl-phenoxy)-1H-benzoimidazole 
• 78765-41-0 2-(2,3-Dimethyl-phenoxy)-1-methyl-1H-benzoimidazole 
• 78765-37-4 2-(2-Chloro-phenoxy)-1-methyl-1H-benzoimidazole 
• 78765-42-1 2-(2,6-Dimethyl-phenoxy)-1-methyl-1H-benzoimidazole 
• 78765-34-1 1-Methyl-2-p-tolyloxy-1H-benzoimidazole 

Relevant articles and documents

Design, Synthesis, and Structural Analysis of Divalent NI Compounds and Identification of a New Electron-Donating Ligand

The dative-bond representation (L→E) in compounds with main group elements (E) has triggered extensive debate in the recent past. The scope and limits of this nonclassical coordination bond warrant comprehensive exploration. Particularly compounds with (L

Synthesis of NHC complexes by oxidative addition of 2-chloro-N- methylbenzimidazole

The oxidative addition of 2-chloro-N-methylbenzimdazole to complexes of type [M(PPh3)4] yields after N-protonation compounds with NH,NMe-substituted NHC ligands. For M = Pd complex compound trans-[3]BF 4 was obtained, while the oxidative addition for M = Pt yielded a mixture of cis-[4]BF4 (major) and trans-[4]BF4 (minor).

Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants

2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).

Structure-Activity Relationship Studies Reveal New Astemizole Analogues Active against Plasmodium falciparum in Vitro

In the context of drug repositioning and expanding the existing structure-activity relationship around astemizole (AST), a new series of analogues were designed, synthesized, and evaluated for their antiplasmodium activity. Among 46 analogues tested, compounds 21, 30, and 33 displayed high activities against asexual blood stage parasites (PfNF54 IC50 = 0.025-0.043 μM), whereas amide compound 46 additionally showed activity against late-stage gametocytes (stage IV/V; PfLG IC50 = 0.6 ± 0.1 μM) and 860-fold higher selectivity over hERG (46, SI = 43) compared to AST. Several analogues displaying high solubility (Sol > 100 μM) and low cytoxicity in the Chinese hamster ovary (SI > 148) cell line have also been identified.

Tuneable Redox Chemistry and Electrochromism of Persistent Symmetric and Asymmetric Azine Radical Cations

Molecular organic radicals have been intensively studied in the last decades, due to their interesting optical, magnetic and redox properties. Here we report the synthesis and characterisation of persistent organic radicals from one-electron oxidation of redox-active azines (RAAs), composed of two guanidinyl or related groups. By connecting two different groups together, asymmetric compounds result. In this way a series of compounds with varying redox potential is obtained that could be oxidised reversibly to the mono- and the dicationic charge states. The accessible redox states were fully determined by chemical redox reactions. The standard Gibbs free energy change for disproportionation of the radical monocation into the dication and the neutral molecule in solution, estimated from cyclovoltammetric measurements, varies between 43 and 71 kJ mol?1. While the neutral RAAs absorb predominately UV light, the radical monocations display strong absorptions covering almost the entire visible region and extending for some compounds into the NIR region. A detailed analysis of this highly reversible electrochromism is presented, and the fast switching characteristics are demonstrated in an electrochromic test device.

Multistage Antiplasmodium Activity of Astemizole Analogues and Inhibition of Hemozoin Formation as a Contributor to Their Mode of Action

A drug repositioning approach was leveraged to derivatize astemizole (AST), an antihistamine drug whose antimalarial activity was previously identified in a high-throughput screen. The multistage activity potential against the Plasmodium parasite's life cycle of the subsequent analogues was examined by evaluating against the parasite asexual blood, liver, and sexual gametocytic stages. In addition, the previously reported contribution of heme detoxification to the compound's mode of action was interrogated. Ten of the 17 derivatives showed half-maximal inhibitory concentrations (IC50s) of 50 100). Screening of AST and its analogues against gametocytes revealed their moderate activity (IC50: 1-5 μM) against late stage P. falciparum gametocytes, while the evaluation of activity against P. berghei liver stages identified one compound (3) with 3-fold greater activity than the parent AST compound. Mechanistic studies showed a strong correlation between in vitro inhibition of β-hematin formation by the AST derivatives and their antiplasmodium IC50s. Analyses of intracellular inhibition of hemozoin formation within the parasite further yielded signatures attributable to a possible perturbation of the heme detoxification machinery.

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