383-08-4

Basic information

• Product Name: 2-(Pentafluoroethyl)benzimidazole
• Synonyms: 2-(PENTAFLUOROETHYL)BENZIMIDAZOLE;2-(perfluoroethyl)-1H-benzo[d]imidazole;2-Perfluoroethyl-1H-benzimidazole
• CAS NO: 383-08-4
• Molecular Formula: C₉H₅F₅N₂
• Molecular Weight: 236.14
• Mol File: 383-08-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 268.6°C at 760 mmHg
• Flash Point: 116.3°C
• Appearance: /
• Density: 1.513g/cm³
• Vapor Pressure: 0.0126mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: 2-(Pentafluoroethyl)benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Pentafluoroethyl)benzimidazole(383-08-4)
• EPA Substance Registry System: 2-(Pentafluoroethyl)benzimidazole(383-08-4)

Safety Data

• Hazardous Substances Data: 383-08-4(Hazardous Substances Data)

Usage

General Description

2-(Pentafluoroethyl)benzimidazole is a chemical compound with the molecular formula C9H5F5N2. It is a substituted benzimidazole derivative, with one pentafluoroethyl group attached to the benzimidazole ring. 2-(Pentafluoroethyl)benzimidazole is primarily used in the pharmaceutical industry as a building block for the synthesis of various drugs and bioactive molecules. It has also been studied for its potential use as an antiviral and antimicrobial agent due to its unique chemical structure and properties. Additionally, 2-(Pentafluoroethyl)benzimidazole has also been investigated for its potential applications in organic electronic materials and as an intermediate in the synthesis of fluorescent dyes. Overall, this compound has a wide range of potential applications in various fields including pharmaceuticals, materials science, and chemical research.

InChI:InChI=1/C9H5F5N2/c10-8(11,9(12,13)14)7-15-5-3-1-2-4-6(5)16-7/h1-4H,(H,15,16)

Upstream product

• 788-67-0 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-2,3-epoxypentane 
• 95-54-5 1,2-diamino-benzene 
• 74728-99-7 trans/cis-dodecafluoro-3,4-epoxyhexane 

Downstream Products

• 49615-25-0 4,5,6,7-tetrachloro-2-pentafluoroethyl-1H-benzimidazole 

Relevant articles and documents

Reactions of perfluoro(2,3-epoxy-2-methylpentane) with o-phenylenediamine and ethylenediamine

Perfluoro(2,3-epoxy-2-methylpentane) reacted with o-phenylenediamine and ethylenediamine via cleavage of the C-C bond to produce 2,2,3,3,3-pentafluoro-N- [2-(2,2,2-trifluoro-1-trifluoromethylethylamino)-phenyl]propanamide and 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)ethyl] -propanamide, respectively. Presumably, these compounds are formed as a result of rearrangement of intermediate ketone generated by intramolecular haloform-type reaction. According to the NMR and X-ray diffraction data, 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)phenyl] propanamide in crystal exists as Z conformer with respect to the amide C-N bond.

Synthesis of 2,3-bis(perfluoroalkyl)quinoxalines and 2,3- bis(perfluoroalkyl)-1,4-benzoxazines from oxides of internal perfluoroolefins

The reactions of oxides of internal trans-, cis-perfluoroolefins with o-phenylenediamine and 2-aminophenol in dioxane gave 2,3-bis(perfluoroalkyl) quinoxalines and 2,3-bis(perfluoroalkyl)-2H-1,4-benzoxazin-2-ols respectively in yields of 23-67%. When N,N-dimethylacetamide was used as a solvent an anionic isomerization of the oxides into ketones, which further yielded 2-(perfluoroalkyl)benzimidazoles in the case of o-phenylenediamine and 2-hydroxy-N-perfluoroalkanoylanilines in the case of 2-aminophenol, became the main path of these reactions. Unusual cyclization resulting in 2-pentafluoroethyl-2-pentafluoropropanoylbenzoxazolidine occurs on interaction between dodecafluoro-3,4-epoxyhexane and 2-aminophenol in N,N-dimethylacetamide.