20034-02-0

Basic information

• Product Name: (6-Methyl-1H-benzimidazol-2-yl)methanol
• Synonyms: CHEMBRDG-BB 4011014;(6-METHYL-1H-BENZOIMIDAZOL-2-YL)-METHANOL;(5-methyl-1H-benzo[d]imidazol-2-yl)methanol;1H-Benzimidazole-2-methanol,5-methyl-(9CI);(5-methyl-1H-benzimidazol-2-yl)methanol;(6-Methyl-1H-benzimidazol-2-yl)methanol;Albb-003795;(6-methyl-1H-benzimidazol-2-yl)methanol(SALTDATA: FREE)
• CAS NO: 20034-02-0
• Molecular Formula: C₉H₁₀N₂O
• Molecular Weight: 162.19
• Product Categories: BENZIMIDAZOLE
• Mol File: 20034-02-0.mol

Chemical Properties

• Melting Point: 203 °C
• Boiling Point: 416.3 °C at 760 mmHg
• Flash Point: 205.6 °C
• Appearance: /
• Density: 1.295 g/cm³
• Vapor Pressure: 1.12E-07mmHg at 25°C
• Refractive Index: 1.69
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.83±0.10(Predicted)
• CAS DataBase Reference: (6-Methyl-1H-benzimidazol-2-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (6-Methyl-1H-benzimidazol-2-yl)methanol(20034-02-0)
• EPA Substance Registry System: (6-Methyl-1H-benzimidazol-2-yl)methanol(20034-02-0)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 20034-02-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(6-Methyl-1H-benzimidazol-2-yl)methanol is used as a pharmacological agent for its potential anti-inflammatory and antioxidant properties, which can contribute to the development of novel drugs targeting various health conditions.
Used in Medicinal Chemistry Research:
(6-Methyl-1H-benzimidazol-2-yl)methanol serves as a valuable building block in the synthesis of bioactive compounds, facilitating the discovery and creation of new therapeutic agents with diverse applications in medicine.
Used in Drug Development:
(6-Methyl-1H-benzimidazol-2-yl)methanol is utilized as a key component in the formulation of new drugs, leveraging its chemical properties to enhance the effectiveness and therapeutic potential of pharmaceutical products.

InChI:InChI=1/C9H10N2O/c1-6-2-3-7-8(4-6)11-9(5-12)10-7/h2-4,12H,5H2,1H3,(H,10,11)

Upstream product

• 79-14-1 glycolic Acid 
• 496-72-0 4-methyl-1,2-diaminobenzene 

Downstream Products

• 1357162-26-5 C₂₁H₂₀N₂O₃ 
• 1357162-35-6 C₂₁H₂₀N₂O₃ 
• 37735-10-7 1,5-dimethyl-1H-benzoimidazole-2-carbaldehyde 
• 68426-72-2 (N-methyl-5-methyl-1H-benzimidazole-2-yl)methanol 
• 80567-68-6 2-(chloromethyl)-5-methyl-1H-benzo[d]imidazole 
• 99459-47-9 5-methyl-1H-benzo[d]imidazole-2-carboxylic acid 
• 155221-51-5 2-(hydroxymethyl)-1,6-dimethylbenzimidazole 
• 883541-93-3 C₉H₈N₂O 

Relevant articles and documents

Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon

D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.

Quinolinones as Inhibitors of Translation Initiation Complex

Provided herein are compounds and pharmaceutical compositions comprising quinolinones. The quinolinones and compositions thereof are useful as eukaryotic translation initiation factor 4F (eIF4F) complex modulators.

Efficient Synthesis and Biological Activity of Novel Indole Derivatives as VEGFR-2 Tyrosine Kinase Inhibitors

A series of novel indole derivatives were synthesized as potent inhibitors for the vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase. Among those, compound 10b demonstrated the highest growth inhibition rate of 66.7% against the VEGFR-2 tyrosine kinase at 10 μM which indicates that indole-benzothiazole might be the favorable structure. The binding mode of compound 10b with VEGFR-2 tyrosine kinase was evaluated by molecular docking.

New (E)-1-alkyl-1H-benzo[d]imidazol-2-yl)methylene)indolin-2-ones: Synthesis, in vitro cytotoxicity evaluation and apoptosis inducing studies

A new series of (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-one derivatives has been synthesized and evaluated for their in vitro cytotoxic activity against a panel of selected human cancer cell lines of prostate (PC-3 and DU-145) and breast (BT-549, MDA-MB-231, MCF-7, 4T1), non-small lung (A549) and gastric (HGC) cancer cells along with normal breast epithelial cells (MCF10A). Among the tested compounds, 8l showed significant cytotoxic activity against MDA-MB-231 and 4T1 cancer cells with IC50values of 3.26 ± 0.24 μM and 5.96 ± 0.67 μM respectively. The compounds 8f, 8i, 8l and 8o were also screened on normal human breast epithelial cells (MCF10A) and found to be safer with lesser cytotoxicity. The treatment of MDA-MB-231 cells with 8l led to inhibition of cell migration ability through disruption of F-actin protein assembly. The flow-cytometry analysis reveals that the cells arrested in G0/G1 phase of the cell cycle. Further, the compound 8l induced apoptosis of MDA-MB-231 cells was characterized by different staining techniques such as Acridine Orange/Ethidium Bromide (AO/EB), DAPI, annexin V-FITC/PI, Rhodamine-123 and MitoSOX red assay. Western blot studies demonstrated that the compound 8l treatment led to activation of caspase-3, increased expression of cleaved PARP, increased expression of pro-apoptotic Bax and decreased expression of anti-apoptotic Bcl-2 in MDA-MB-231 cancer cells.

Synthesis and antinociceptive activity of meperidine-like benzimidazole derivatives

(Graph presented) A series of novel benzimidazole derivatives have been prepared and characterized by IR, 1H-NMR spectroscopic data and elemental analysis. All the final compounds were screened for their antinociceptive activities with tail flick test. Among the synthesized compounds 3a, 4a, 4c, 8a, 9a exhibited significant antinociceptive activity. Compound 9a was found to have the highest antinociceptive activity at both 60 minutes and 120 minutes. Additionally, compounds 3a, 4a, 8a and 9a showed naloxone-reversible antinociceptive activity.

Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi

A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.

Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents

A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds have some common features; three possess 5-halo substituents; two are derivatives of (S)-2-ethanaminebenzimidazole; and the others are derivatives of one 2-(chloromethyl)-1Hbenzo[ d]imidazole and (1H-benzo[d]imidazol-2-yl)methanethiol. The results from the antifungal screening were also very interesting: 23 compounds exhibited potent fungicidal activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives could be considered promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications.

One-Pot Base-Mediated Synthesis of Functionalized Aza-Fused Polycyclic Quinoline Derivatives

A new one-pot protocol has been developed for the facile and efficient synthesis of aza-fused polycyclic quinolines (e.g., pyrrolo[1,2-a]quinolines) by the base-catalyzed reaction of 2-formylpyrroles and 2-halophenylacetonitriles. This reaction proceeded under transition metal-free conditions and showed high functional group tolerance, with the desired products being formed in good yields.

Synthesis of substituted benzimidazolyl curcumin mimics and their anticancer activity

A novel curcumin mimic library (14a-14h and 15a-15h) possessing variously substituted benzimidazole groups was synthesized through the aldol reaction of (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (7) or (E)-4-(3-hydroxy-4- methoxyphenyl)but-3-en-2-one (13) with diversely substituted benzimidazolyl-2-carbaldehyde (12a-12h). The MTT assay of the cancer cells MCF-7, SH-SY5Y, HEP-G2, and H460 showed that compound 14c with IC50 of 1.0 and 1.9 μM has a strong inhibitory effect on the growth of SH-SY5Y and Hep-G2 cells, respectively, and that compound 15h with IC50 of 1.9 μM has a strong inhibitory effect on the growth of MCF-7 cancer cells.