6953-65-7

Basic information

• Product Name: (5-chloro-1H-benzo[d]imidazol-2-yl)methanol
• Synonyms: (5-chloro-1H-benzo[d]imidazol-2-yl)methanol;1H-Benzimidazole-2-methanol,5-chloro-(9CI);(5-chloro-1H-benzimidazol-2-yl)methanol(SALTDATA: 0.06NH4Cl);(6-Chloro-1H-benzo[d]iMidazol-2-yl)Methanol;2-Benzimidazolemethanol, 5-chloro-;5-Chloro-2-hydroxymethylbenzimidazole;Benzimidazole, 5-chloro-2-hydroxymethyl-;(6-Chloro-1H-benzo[d]imidazol-2-yl)
• CAS NO: 6953-65-7
• Molecular Formula: C₈H₇ClN₂O
• Molecular Weight: 182.60698
• Product Categories: BENZIMIDAZOLE
• Mol File: 6953-65-7.mol

Chemical Properties

• Melting Point: 205 °C
• Boiling Point: 443.9°C at 760 mmHg
• Flash Point: 222.2°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 1.17E-08mmHg at 25°C
• Refractive Index: 1.724
• Storage Temp.: 2-8°C
• PKA: 10.17±0.10(Predicted)
• CAS DataBase Reference: (5-chloro-1H-benzo[d]imidazol-2-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (5-chloro-1H-benzo[d]imidazol-2-yl)methanol(6953-65-7)
• EPA Substance Registry System: (5-chloro-1H-benzo[d]imidazol-2-yl)methanol(6953-65-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6953-65-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5-chloro-1H-benzo[d]imidazol-2-yl)methanol is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows it to be a key component in the creation of new drug candidates, potentially leading to novel treatments for a range of diseases and conditions.
Used in Drug Discovery and Development:
As a building block in the synthesis of biologically active molecules, (5-chloro-1H-benzo[d]imidazol-2-yl)methanol is used in drug discovery and development to explore new chemical entities with potential therapeutic applications. Its reactivity and structural features make it a promising candidate for the design of innovative pharmaceutical agents.
Used in Material Science:
(5-chloro-1H-benzo[d]imidazol-2-yl)methanol may have applications in material science due to its unique chemical properties. Its potential use in this field could involve the development of new materials with specific characteristics, such as improved stability or reactivity.
Used in Organic Chemistry:
In the field of organic chemistry, (5-chloro-1H-benzo[d]imidazol-2-yl)methanol serves as a valuable tool for researchers. Its reactivity and structural features can be leveraged in various organic synthesis processes, contributing to the advancement of chemical knowledge and the development of new organic compounds.

InChI:InChI=1/C8H7ClN2O/c9-5-1-2-6-7(3-5)11-8(4-12)10-6/h1-3,12H,4H2,(H,10,11)

Upstream product

• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 79-14-1 glycolic Acid 

Downstream Products

• 7118-63-0 2-benzyl-5-chloro-1H-benzo[d]imidazole 
• 380177-22-0 (N-methyl-5-chloro-1H-benzimidazole-2-yl)methanol 
• 156212-80-5 5-chloro-1-methyl-1H-benzimidazole-2-carbaldehyde 
• 1357162-39-0 C₂₀H₁₇ClN₂O₃ 
• 1357162-30-1 C₂₀H₁₇ClN₂O₃ 
• 39811-14-8 5-chloro-1H-benzimidazole-2-carboxylic acid 
• 20443-38-3 5-chloro-2-(chloromethyl)-1H-benzo[d]imidazole 

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.

Reactions of 2-carbonyl- And 2-hydroxy(or methoxy)alkylsubstituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species

Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkylbenzimidazoles with arenes in the Br?nsted superacid TfOH resulted in the formation of the corresponding Friedel-Crafts reaction products, 2-diarylmethyl and 2-arylmethyl-substituted benzimidazoles, in yields up to 90%. The reaction intermediates, protonated species derived from starting benzimidazoles in TfOH, were thoroughly studied by means of NMR and DFT calculations and plausible reaction mechanisms are discussed.

Design, synthesis and biological evaluation of benzimidazole-rhodanine conjugates as potent topoisomerase II inhibitors

In this study, a series of benzimidazole-rhodanine conjugates were designed, synthesized and investigated for their topoisomerase II (Topo II) inhibitory and cytotoxic activities. The results from Topo II-mediated pBR322 DNA relaxation and cleavage assays showed that the synthesized compounds might act as Topo II catalytic inhibitors. Certain compounds displayed potent Topo II inhibition at 10 μM. The cytotoxic activities of these compounds against HeLa, A549, Raji, PC-3, MDA-MB-201, and HL-60 cancer cell lines were evaluated. The results indicated that these compounds exhibited strong antiproliferative activity. A good relationship was observed between the Topo II inhibitory potency and the cytotoxicity of these compounds. The structure-activity relationship revealed that the electronic effects, the phenyl group, and the rhodanine moiety were particularly important for the Topo II inhibitory potency and cytotoxicity.

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.

SPIRO UREA COMPOUNDS AS RSV ANTIVIRAL COMPOUNDS

The invention concerns novel substituted spiro urea azetidinyl or piperidinyl compounds of formula (I) having antiviral activity, in particular, having an inhibitory activity on the replication of the respiratory syncytial virus (RSV). The invention furth

RSV ANTIVIRAL COMPOUNDS

Inhibitors of RSV replication of formula RI including stereochemically isomeric forms, and salts or solvates thereof, wherein R22, W, Q, V, Z p,s,and Het have the meaning as defined herein. The present invention also relates to processes for preparing said compounds, pharmaceutical compositions containing them and their use, alone or in combination with other RSV inhibitors, in RSV therapy.

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.

HETEROCYCLIC COMPOUNDS

Certain thienopyrrolyl and furanopyrrolyl compounds are disclosed as useful to treat or prevent disorders and conditions mediated by the histamine H4 receptor, including allergic rhinitis.

Synthesis and insecticidal activity of some benzimidazolic and benzothiazolic derivatives

The benzimidazolic and benzothiazolic derivatives with a (CH2)n radical in 2 position of the heterocycle had been synthesized and then tested for their insecticidal activity on Culex pipiens larvae. The benzothiazolic derivatives were found to be the most active. The study has also showed that this activity was related to the nature of the substitute in 2 position of the heterocycle. This activity increased when (CH2)n chain increased until n = 6; above this value, the activity decreased.