312-73-2

Basic information

• Product Name: 2-(Trifluoromethyl)benzimidazole
• Synonyms: 2-(TRIFLUOROMETHYL)-1H-BENZIMIDAZOLE;2-(TRIFLUOROMETHYL)-1H-BENZO[D]IMIDAZOLE;2-(TRIFLUOROMETHYL)BENZIMIDAZOLE;2-(trifluoromethyl)-1h-benzimidazol;2-trifluoromethyl-benzimidazol;RARECHEM AQ NN 0072;3-TRIFLUOROMETHYL BENZIMIDAZOLE;1H-Benzimidazole,2-(trifluoromethyl)-(9CI)
• CAS NO: 312-73-2
• Molecular Formula: C₈H₅F₃N₂
• Molecular Weight: 186.13
• Product Categories: BENZIMIDAZOLE;Imidazol&Benzimidazole;Benzimidazoles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 312-73-2.mol

Chemical Properties

• Melting Point: 208-211 °C(lit.)
• Boiling Point: 262.8 °C at 760 mmHg
• Flash Point: 112.7 °C
• Appearance: /
• Density: 1.3658 (estimate)
• Vapor Pressure: 0.000137mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.25±0.10(Predicted)
• Water Solubility: PRACTICALLY INSOLUBLE
• CAS DataBase Reference: 2-(Trifluoromethyl)benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Trifluoromethyl)benzimidazole(312-73-2)
• EPA Substance Registry System: 2-(Trifluoromethyl)benzimidazole(312-73-2)

Safety Data

• Hazard Codes: T,Xi
• Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36/37/39-45-28A
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: DE1576000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 312-73-2(Hazardous Substances Data)

Usage

Chemical Properties

light grey fine powder

Uses

Agricultural chemical.

Hazard

A poison by ingestion.

InChI:InChI=1/C8H7ClO4S/c1-13-8(10)6-2-4-7(5-3-6)14(9,11)12/h2-5H,1H3

Upstream product

• 51-17-2 benzoimidazole 
• 2314-97-8 iodotrifluoromethane 
• 59938-06-6 (E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one 
• 95-54-5 1,2-diamino-benzene 
• 109317-75-1 4-trifluoroacetyl-2,3-dihydrofuran 
• 109317-74-0 1-(3,4-dihydro-2H-5-pyranyl)-2,2,2-trifluoro-1-ethanone 
• 773-29-5 trans/cis-octafluoro-2,3-epoxybutane 
• 844444-24-2 1,1,1,5,5,5-hexafluoropentane-2,3,4-trione-3-(p-tolyl)hydrazone 
• 174906-23-1 5-trifluoroacetyltricyclo<4.3.1.1^3,8>undecan-4-one 

Downstream Products

• 327-19-5 5-nitro-2-(trifluoromethyl)-1H-benzo[d]imidazole 
• 609342-46-3 Acetic acid (1S,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(2-trifluoromethyl-benzoimidazol-1-ylmethoxy)-cyclohexyl ester 
• 847235-55-6 2-trifluoromethyl-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole 
• 884069-78-7 1-(4-nitrophenyl)-2-(trifluoromethyl)-1H-benzo[d]imidazole 
• 2338-29-6 4,5,6,7-Tetrachlor-2-trifluormethyl-benzimidazol 
• 139591-04-1 1-propargyl-2-trifluoromethyl-1H-benzoimidazole 
• 30049-07-1 1-ethyl-2-trifluoromethylbenzimidazole 
• 1016257-74-1 C₁₇H₁₃F₃N₂O₂ 
• 1074766-25-8 C₁₅H₁₀BrF₃N₂O 
• 1074766-24-7 C₁₅H₁₁F₃N₂O 
• 880177-56-0 4-(2-trifluoromethyl-benzoimidazol-1-yl)-benzaldehyde 
• 911381-01-6 ethyl 2-ethoxy-3-(4-{2-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]ethoxy}phenyl)propanoate 
• 119295-20-4 Benzoic acid 1-acetoxymethyl-2-(2-trifluoromethyl-benzoimidazol-1-ylmethoxy)-ethyl ester 

Relevant articles and documents

Reactions of epoxides derived from internal perfluoroolefins with o-phenylenediamine and 2-aminophenol

The reactions of epoxy derivatives of internal perfluoroolefins with o-phenylenediamine and 2-aminophenol in dioxane gave 23-67% of the corresponding 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis-(perfluoroalkyl)-2H-1,4- benzoxazin-2-ols, respectively. When N,N-dimethylacetamide was used as a solvent, the main reaction pathway was anionic isomerization of epoxides into ketones which were then converted into 2-perfluoroalkylbenzimidazoles (in the reactions with o-phenylenediamine) or 2-hydroxy-N-perfluoroalkanoylanilines (in the reactions with 2-aminophenol). The reaction of 3,4-epoxydodecafluorohexane with 2-aminophenol in N,N-dimethylacetamide was accompanied by unusual cyclization to afford 2-pentafluoropropanoyl-2-pentafluoroethyl-1,3- benzoxazolidine. Pleiades Publishing, Inc., 2006.

The interaction of fluorinated 2-arylhydrazono-1,3-dicarbonyl compounds with o-phenylenediamine

2-Arylhydrazono-3-fluoroaklyl-3-oxo esters react with o-phenylenediamine under neutral conditions to form mainly o-aminoanilides, from which can be obtained 1,5-benzodiazepin-2-ones. Ethyl-2-(benzimidazol-2-yl)-2-(4-methylphenyl)hydrazonoethanoate was isolated also from the reaction of di(tri)fluoromethyl-containing 2-arylhydrazono-3-oxo esters. The reactions of o-phenylenediamine with 1,2,3-triketone 2-arylhydrazones containing alkyl substituents result in the formation of 1-(benzimidazol-2-yl)-1,2-dioxoalkane arylhydrazones, whereas phenylsubstituted analogues afford 2-phenylbenzimidazole. Nickel(II) chelates of N, N ′-phenylene-bis(2-arylazo-1,3-aminovinylketones) were obtained from 1,2,3-triketone 2-arylhydrazones and o-phenylenediamine using a template method.

A novel method for preparation of trifluoromethyl substituted 2,3- dihydro-1,4-diazepine and benzimidazole

Ethylenediamine reacted readily with 4-ethoxy-1,1,1-trifluoro-3-butene- 2-one to form 5-trifluoromethyl-2,3-dihydro-1,4-diazepine in good yield. Under the same reaction conditions o-phenylene diamine gave 2-trifluoromethyl benzimidazole and benzimidazole.

Heterocyclization of 5-trifluoroacetyltricyclo-[4.3.1.13,8]undecan-4-one to some 6- and 7-membered nitrogen heterocycles

Heterocyclization study of 5-trifluoroacetyl[4.3.1.13,8]undecan-4-one into pyrimidine, pyridine, and 1,4-diazepine derivatives as a route to trifluoromethylated homoadamantanefused 6- and 7-membered nitrogen heterocyctes is reported.

Photochemical Perfluoroalkylation of Imidazoles

Imidazole and its derivatives undergo facile trifluoromethylation or perfluoroalkylation, in methanol solution at ambient temperature, following radical dissociation of RFI by γ or UV irradiation.In the case of imidazole, attack occurs preferen