559-37-5

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-(Heptafluoropropyl)benzimidazole is used as a building block for the synthesis of various pharmaceuticals and agrochemicals, leveraging its unique fluorinated structure to enhance the properties and efficacy of the final products.
Used in Materials Science:
In the field of materials science, 2-(Heptafluoropropyl)benzimidazole is utilized in the development of fluorinated polymers and coatings, capitalizing on its fluorinated structure to improve the performance and durability of these materials.
Used as a Corrosion Inhibitor:
2-(Heptafluoropropyl)benzimidazole is used as a potential corrosion inhibitor, taking advantage of its ability to form a protective film on metal surfaces, thereby preventing corrosion and extending the service life of metal components.

InChI:InChI=1/C10H5F7N2/c11-8(12,9(13,14)10(15,16)17)7-18-5-3-1-2-4-6(5)19-7/h1-4H,(H,18,19)

Synthetic route

heptafluorobutyric Acid (375-22-4) + 1,2-diamino-benzene (95-54-5) → 2-heptafluoropropyl-1H-benzoimidazole (559-37-5)

Conditions	Yield
at 120℃; for 4h;	90%
In neat (no solvent) at 120℃; for 4h; Product distribution; further perfluoroalkanecarboxylic acids or anhydrides; presence of polyphosphoric acid; variation of temperature and time;	90%
With hydrogenchloride In benzene for 16h; Heating;	32%
With hydrogenchloride

1,2-epoxy-1,1,2,3,3,4,4,4-octafluorobutane (3709-90-8) + 1,2-diamino-benzene (95-54-5) → 2-heptafluoropropyl-1H-benzoimidazole (559-37-5) + 3-pentafluoroethyl-2(1H)-quinoxalinone (89995-28-8)

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether at 20℃; for 3h;	A n/a B 78%

2-Acetyl-4,4,5,5,6,6,6-heptafluoro-3-oxo-hexanoic acid ethyl ester (115479-06-6) + 1,2-diamino-benzene (95-54-5) → 2-heptafluoropropyl-1H-benzoimidazole (559-37-5) + ethyl acetoacetate (141-97-9)

Conditions	Yield
In ethanol for 4h; Heating;	A 74% B n/a

trans/cis-dodecafluoro-3,4-epoxyhexane (74728-99-7) + 1,2-diamino-benzene (95-54-5) → 2,3-bis(pentafluoroethyl)quinoxaline + 2-(1,1,2,2,2-pentafluoroethyl)-1H-benzimidazole (383-08-4) + 2-heptafluoropropyl-1H-benzoimidazole (559-37-5) + 3-pentafluoroethyl-2(1H)-quinoxalinone (89995-28-8)

Conditions	Yield
In N,N-dimethyl acetamide for 2.5h; Heating;	A 4.4% B 52% C n/a D n/a
Stage #1: trans/cis-dodecafluoro-3,4-epoxyhexane; 1,2-diamino-benzene In N,N-dimethyl acetamide at 100℃; for 2.5h; Stage #2: With water In N,N-dimethyl acetamide cooling; Further byproducts given;	A 4.4% B 52% C n/a D n/a

1,2-diamino-benzene (95-54-5) + 1-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexene → 2-heptafluoropropyl-1H-benzoimidazole (559-37-5)

Conditions	Yield
With triethylamine In ethanol	49%

2-heptafluoropropyl-1H-benzoimidazole (559-37-5) → 4,5,6,7-tetrachloro-2-heptafluoropropyl-1H-benzimidazole (1410095-92-9)

Conditions	Yield
With hydrogenchloride; nitric acid In water at 60℃; for 28h; Reflux;	71%

2-heptafluoropropyl-1H-benzoimidazole (559-37-5) → 4,5,6,7-Tetrabromo-2-heptafluoropropylbenzimidazole

Conditions	Yield
With bromine In water for 24h; Heating;	55%

Upstream product

• 375-22-4 heptafluorobutyric Acid 
• 95-54-5 1,2-diamino-benzene 
• 3709-90-8 1,2-epoxy-1,1,2,3,3,4,4,4-octafluorobutane 
• 74728-99-7 trans/cis-dodecafluoro-3,4-epoxyhexane 
• 115479-06-6 2-Acetyl-4,4,5,5,6,6,6-heptafluoro-3-oxo-hexanoic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis and structure of reaction products obtained from 1,2-epoxyperfluorobutane and bifunctional nucleophilic reagents

1,2-Epoxyperfluorobutane readily reacts with bifunctional nucleophilic reagents to provide heterocyclic compounds with a pentafluoroethyl substituent. The reaction of this epoxide with thiourea and acetone thiosemicarbazone gave rise to 2-amino-5-pentaflu

Reaktionen terminaler Perfluoroalkene mit Diaminen und Diphenolen

Model compounds related to the reaction products of perfluooalkenes produced by the electron-beam irradiation of poly(tetrafluoroethylene) with dinucleophilic reactants have been synthesized.Such model compounds, in reaction with diphenols or diamines, give information relating to the mechanism of crosslinking reactions.Results obtained with perfluorohept-1-ene show that terminal perfluoroalkenes react preferentially with dinucleophilic reactants to give unsaturated ether and amine structures.

A Novel Synthesis of 5-Perfluoroalkyl-2,3-dihydro-1,4-diazepines from 1-Perfluoroalkyl-2-iodoethylenes

A novel method for the synthesis of 5-perfluoroalkyl-2,3-dihydro-1,4- diazepines using easily available starting materials is described. 1-Perfluoroalkyl-2-iodoethylenes, obtained from the reaction of perfluoroalkyl iodides and alkynes, reacted with ethylenediamine under mild conditions to give the title compounds in good yields. A possible mechanism is proposed.

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.

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.

SYNTHESIS OF SOME BENZIMIDAZOLES CONTAINING 2-PERFLUORO SUBSTITUENTS

A new method is described for the preparation of 2-perfluoroalkylether-benzimidazoles through the N-monoacyl derivatives of o-phenylenediamine. 2-Pentafluorophenylbenzimidazole has been obtained by the reaction of o-phenylenediamine and pentafluorobenzoic acid in the presence of polyphosphoric acid. 2-Perfluoroalkylbenzimidazoles have been prepared in excellent yields by direct condensation of o-phenylenediamine with perfluoroalkane-carboxylic acids in the absence of any solvent or added reagent.Some derivatives of these compounds are also described.