683240-76-8

Basic information

• Product Name: 5-BROMO-2-CHLORO-1H-BENZIMIDAZOLE
• Synonyms: 5-BROMO-2-CHLORO-1H-BENZIMIDAZOLE;5-BroMo-2-chloro-1H-benzo[d]iMidazole;6-Bromo-2-chloro-1H-benzoimidazole;5-Bromo-2-chlorobenzimidazole
• CAS NO: 683240-76-8
• Molecular Formula: C₇H₄BrClN₂
• Molecular Weight: 231.49
• Mol File: 683240-76-8.mol

Chemical Properties

• Melting Point: 212-213°
• Boiling Point: 387.32 °C at 760 mmHg
• Flash Point: 188.044 °C
• Appearance: /
• Density: 1.878
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.73
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.56±0.10(Predicted)
• CAS DataBase Reference: 5-BROMO-2-CHLORO-1H-BENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-CHLORO-1H-BENZIMIDAZOLE(683240-76-8)
• EPA Substance Registry System: 5-BROMO-2-CHLORO-1H-BENZIMIDAZOLE(683240-76-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 683240-76-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-2-chloro-1H-benzimidazole is used as a potential anti-cancer agent for its potential to target and treat cancer cells. Its specific mechanism of action and efficacy in combating cancer are areas of ongoing research.
Used in Chemical Synthesis:
In the chemical synthesis industry, 5-Bromo-2-chloro-1H-benzimidazole serves as a building block for the creation of various pharmaceuticals and agrochemicals. Its unique structure allows it to be a valuable component in the development of new compounds with specific therapeutic or pesticidal properties.
Used in Research and Development:
5-Bromo-2-chloro-1H-benzimidazole is utilized in research and development settings to explore its potential applications and to understand its interactions with biological systems. This can lead to the discovery of new uses and mechanisms of action for 5-Bromo-2-chloro-1H-benzimidazole in medicine and other fields.
Safety Considerations:
While 5-Bromo-2-chloro-1H-benzimidazole has potential applications, it is important to handle it with caution due to its potential to cause skin and eye irritation. Proper safety measures, such as wearing protective gear and working in a controlled environment, should be taken to minimize risks associated with its use.

InChI:InChI=1/C7H4BrClN2/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H,(H,10,11)

Upstream product

• 39513-26-3 5-bromo-1,3-dihydro-benzoimidazol-2-one 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 4857-06-1 2-chloro-1H-benzoimidazole 

Downstream Products

• 1033624-95-1 (5-bromo-1H-benzoimidazol-2-yl)-(4-trifluoromethyl-benzyl)-amine 
• 1073558-66-3 8-(5-bromo-1H-benzimidazol-2-yl)-3-phenyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one 
• 1453097-58-9 C₁₈H₁₅BrN₄O 
• 54303-63-8 C₇H₇BrN₄ 
• 808127-74-4 5-bromo-N-phenyl-1H-benzo[d]imidazol-2-amine 
• 1416334-91-2 2,4-difluoro-N-[2-(methyloxy)-5-(2-{[2-(4-morpholinyl)ethyl]amino}-1H-benzimidazol-5-yl)-3-pyridinyl]benzenesulfonamide 
• 1416334-92-3 2,4-difluoro-N-[2-(methyloxy)-5-(2-{[2-(1-pyrrolidinyl)ethyl]amino}-1H-benzimidazol-5-yl)-3-pyridinyl]benzenesulfonamide 
• 1359858-97-1 C₁₇H₁₆BrN₃O 

Relevant articles and documents

A α 7 smoke alkali acetylcholine receptor ligand and its preparation method

The present invention relates to an alpha7 nicotinic acetylcholine receptor ligand and a preparation method thereof. The ligand includes an agonist and an imaging agent, the agonist is a 1,4-diazabicyclo [3.2.2] nonane-benzo heterocyclic derivative, and the imaging agent is 125I and 18F-trifluoromethyl marker. The derivatives both have good brain uptake, the absorption values in different regions of the brain are basally consistent with the distribution of alpha7nAChR receptors, the uptake of the derives is highest in hippocampus, thalamus, cortex and other regions where the alpha7nAChR receptors targetedly distribute, and the derives can be blocked by known alpha7nAChR ligands but can not be blocked by alpha4beta2 medicine. Therefore, the 1,4-diazabicyclo [3.2.2] nonane-benzo heterocyclic derivative and the 125I and 18F-trifluoromethyl marker are potential agonist and imaging agent for alpha7 nicotinic acetylcholine receptors.

Discovery of a Selective Aurora A Kinase Inhibitor by Virtual Screening

Here we report the discovery of a selective inhibitor of Aurora A, a key regulator of cell division and potential anticancer target. We used the atom category extended ligand overlap score (xLOS), a 3D ligand-based virtual screening method recently developed in our group, to select 437 shape and pharmacophore analogs of reference kinase inhibitors. Biochemical screening uncovered two inhibitor series with scaffolds unprecedented among kinase inhibitors. One of them was successfully optimized by structure-based design to a potent Aurora A inhibitor (IC50 = 2 nM) with very high kinome selectivity for Aurora kinases. This inhibitor locks Aurora A in an inactive conformation and disrupts binding to its activator protein TPX2, which impairs Aurora A localization at the mitotic spindle and induces cell division defects. This phenotype can be rescued by inhibitor-resistant Aurora A mutants. The inhibitor furthermore does not induce Aurora B specific effects in cells.

2-AMINO-BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS 5-LIPOXYGENASE AND/OR PROSTAGLANDIN E SYNTHASE INHIBITORS

The present invention relates to benzimidazole derivatives having the general formula I, wherein n is 0 or 1; X1 and X2 are independently, at each occurrence, CR5 or N; Y is C1-C6 alkylene, wherein alkylene is optionally substituted with one to two C1-C3 alkyl groups; R1 is selected from the group consisting of hydrogen, halogen, C1-C6 alkoxy, -NH2, -NHR6, -NR7R8 and -NH-(R9)n-R10, n being 0 or 1; R2 is selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, -NH2, -NHR6, - NR7R8 and -NH-(R9)n-R10; R3 is selected from the group consisting of hydrogen, hydroxyl, OR11, -NR7R8, C1-C6 alkoxy, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C3 haloalkyl, -C(O)NHR11, aryl, heteroaryl and heterocyclyl, wherein each of said cycloalkyl, aryl, heteroaryl and heterocyclyl is optionally and independently substituted with one to four Ra groups; and R4 is selected from the group consisting of -NH2, -N(R12)(V)pR13, - NH(V)p-OR14, -NHC(O)R15, and groups of formula la shown below, and their use in the treatment of diseases, in particular inflammatory diseases, cancer, stroke and/or Alzheimer's disease.

Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs

A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5- methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects.

Design, syntheses, and structure-activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives

Design, syntheses, and structure-activity relationships of a novel class of 2-{3-oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright

PROTEIN KINASE INHIBITORS

Compounds that inhibit protein kinases, compositions containing the compounds and methods of treating diseases using the compounds are disclosed.

Design of potent, orally available antagonists of the transient receptor potential vanilloid 1. Structure-activity relationships of 2-piperazin-1-yl-1H- benzimidazoles

The vanilloid receptor-1 (VR1 or TRPV1) is a membrane-bound, nonselective cation channel that is predominantly expressed by peripheral neurons sensing painful stimuli. TRPV1 antagonists produce antihyperalgesic effects in animal models of inflammatory and neuropathic pain. Herein, we describe the synthesis and the structure-activity relationships of a series of 2-(4-pyridin-2- ylpiperazin-1-yl)-1H-benzo-[d]imidazoles as novel TRPV1 antagonists. Compound 46ad was among the most potent analogues in this series. This compound was orally bioavailable in rats and was efficacious in blocking capsaicin-induced flinch in rats in a dose-dependent manner. Compound 46ad also reversed thermal hyperalgesia in a model of inflammatory pain, which was induced by complete Freund's adjuvant (CFA).

BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS

Compounds of formula (I) are useful in the treatment of vanilloid-receptor-meditated diseases, such as inflammatory or neuropathic pain and diseases involving sensory nerve function such as asthma, rheumatoid arthritis, osteoarthritis, inflammatory bowel disorders, urinary incontinence, migraine and psoriasis.