89457-09-0

Basic information

• Product Name: Ethyl 2-(trifluoromethyl)-1H-1,3-benzodiazole-5-carboxylate
• Synonyms: Ethyl 2-(trifluoromethyl)-1H-1,3-benzodiazole-5-carboxylate
• CAS NO: 89457-09-0
• Molecular Formula: C₁₁H₉F₃N₂O₂
• Molecular Weight: 258.1965696
• Mol File: 89457-09-0.mol

Chemical Properties

• Boiling Point: 352.4°Cat760mmHg
• Flash Point: 166.9°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 3.85E-05mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: Ethyl 2-(trifluoromethyl)-1H-1,3-benzodiazole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-(trifluoromethyl)-1H-1,3-benzodiazole-5-carboxylate(89457-09-0)
• EPA Substance Registry System: Ethyl 2-(trifluoromethyl)-1H-1,3-benzodiazole-5-carboxylate(89457-09-0)

Safety Data

• Hazardous Substances Data: 89457-09-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H9F3N2O2/c1-2-18-9(17)6-3-4-7-8(5-6)16-10(15-7)11(12,13)14/h3-5H,2H2,1H3,(H,15,16)

Upstream product

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• 64-17-5 ethanol 
• 82791-93-3 2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carboxylic acid 
• 619-05-6 3,4-diaminobenzoic acid 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 

Relevant articles and documents

Fe(OTf)3-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles from o-arylenediamines and hexafluoroacetylacetone

An iron-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles through condensation of o-arylenediamines and hexafluoroacetylacetone followed by intramolecular addition and C–C bond cleavage in one-pot has been developed. A series of title compounds were obtained with up to 99% yield. This method is quite practical and suitable for scalable preparation due to simple experimental procedure and readily available reagents.

Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives

Novel 4″-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4″ bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the mef gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4″-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4″-O-(2-alkyl)benzimidazolyl derivatives.

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A benzimidazole compound represented by the formula (I): wherein R3is a carboxyl group, a esterified carboxyl group, an amidated carboxyl group, an amino group, an amido group, or a sulfonyl group, or their pharmaceutically acceptable salts. Because of their blood sugar-depressing effect or PDE5 inhibitory effect, these compounds or salts thereof are useful as medicines for treating impaired glucose tolerance, diabetes, diabetic complications, syndrome of insulin resistance, hyperlipidemia, atherosclerosis, cardiovascular disorders, hyperglycemia, or hypertension; or stenocardia, hypertension, pulmonary hypertension, congestive heart failure, glomerulopathy, tubulointerstitial disorders, renal failure, atherosclerosis, angiostenosis, distal angiopathy, cerebral apoplexy, chronic reversible obstructions, allergic rhinitis, urticaria, glaucoma, diseases characterized by enteromotility disorders, impotence, diabetic complications, nephritis, cancerous cachexia, or restenosis after PTCA.

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Full length article

Cyclocondensation of N-(carbotrifluoromethyl)-ortho-arylenediamines leads to a series of 2-trifluoromethylarylimidazoles with good yields on montmorillonite K10 in 'dry media' under microwave irradiation within 2 min in a domestic oven. By conventional heating in the same conditions, no reaction is observed.

Benzimidazole derivatives

PCT No. PCT/JP96/03858 Sec. 371 Date Nov. 2, 1998 Sec. 102(e) Date Nov. 2, 1998 PCT Filed Dec. 27, 1996 PCT Pub. No. WO97/24334 PCT Pub. Date Jul. 10, 1997Novel benzimidazole derivatives represented by the formula (I): wherein R3 is a carboxyl group, a esterified carboxyl group, an amidated carboxyl group, an amino group, an amido group, or a sulfonyl group, or their pharmaceutically acceptable salts. Because of their blood sugar-depressing effect or PDE5 inhibitory effect, these compounds or salts thereof are useful as medicines for treating impaired glucose tolerance, diabetes, diabetic complications, syndrome of insulin resistance, hyperlipidemia, atherosclerosis, cardiovascular disorders, hyperglycemia, or hypertension; or stenocardia, hypertension, pulmonary hypertension, congestive heart failure, glomerulopathy, tubulointerstitial disorders, renal failure, atherosclerosis, angiostenosis, distal angiopathy, cerebral apoplexy, chronic reversible obstructions, allergic rhinitis, urticaria, glaucoma, diseases characterized by enteromotility disorders, impotence, diabetic complications, nephritis, cancerous cachexia, or restenosis after PTCA.