155221-51-5

Basic information

• Product Name: 1H-Benzimidazole-2-methanol,1,6-dimethyl-(9CI)
• Synonyms: 1H-Benzimidazole-2-methanol,1,6-dimethyl-(9CI);(1,6-Dimethyl-1H-benzo[d]imidazol-2-yl)methanol
• CAS NO: 155221-51-5
• Molecular Formula: C10H12N2O
• Molecular Weight: 176.21508
• Product Categories: BENZIMIDAZOLE
• Mol File: 155221-51-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Benzimidazole-2-methanol,1,6-dimethyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-2-methanol,1,6-dimethyl-(9CI)(155221-51-5)
• EPA Substance Registry System: 1H-Benzimidazole-2-methanol,1,6-dimethyl-(9CI)(155221-51-5)

Safety Data

• Hazardous Substances Data: 155221-51-5(Hazardous Substances Data)

Upstream product

• 79-14-1 glycolic Acid 
• 55783-45-4 3-(methylamino)-4-aminotoluene dihydrochloride salt 
• 578-46-1 5-methyl-2-nitroaniline 
• 155221-62-8 5-methyl-2-nitrotrifluoroacetanilide 
• 65081-42-7 3-(N-methylamino)-4-nitrotoluene 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 20034-02-0 (5-methyl-1H-benzimidazole-2-yl)methanol 
• 74-88-4 methyl iodide 
• 20034-02-0 (6-methyl-1H-benzoimidazol-2-yl)methanol 
• 77-78-1 dimethyl sulfate 

Relevant articles and documents

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.

Structure-Activity Studies of Benzimidazole-Based DNA-Cleaving Agents. Comparison of Benzimidazole, Pyrrolobenzimidazole, and Tetrahydropyridobenzimidazole Analogues

The synthesis and cytotoxic properties of benzimidazole-based DNA-cleaving agents are presented herein.These agents include pyrrolobenzimidazole (PBI), benzimidazole (BI), and tetrahydropyridobenzimidazole (TPBI) analogues.As a result of these studies, it is concluded that the pyrrolo ring is not necessary for cytotoxicity (PBI is only slightly more cytotoxic than BI) but that homologation of the pyrrolo ring by one carbon results in a system, TPBI, prone to decomposition.Another conclusion is that the 6-aziridinyl derivative of the PBI system is more potent than the 7-aziridinyl derivative.Comparative studies with known antitumor agents revealed that the benzimidazole-based DNA-cleaving agents possess a unique spectrum of activity.Noteworthy observations are the high level of cytotoxicity against melanoma cell lines and the complete absence of activity against leukemia cell lines.The reductive activation and DNA-cleavage properties of the most active analogue (BI-A) are also presented.Reduction of the quinone ring to the hydroquinone results in nucleophile and proton trapping by the aziridinyl group.Documented nucleophiles include water and the oxygen anion of 5'-dAMP.In addition, reduced BI-A reacts with DNA to form a stable adduct, which cleaves at G + A bases upon heating in basic gel-loading solution.