559-37-5

Basic information

• Product Name: 2-(HEPTAFLUOROPROPYL)BENZIMIDAZOLE
• Synonyms: 2-(HEPTAFLUORO-N-PROPYL)BENZIMIDAZOLE;2-(HEPTAFLUOROPROPYL)BENZIMIDAZOLE
• CAS NO: 559-37-5
• Molecular Formula: C₁₀H₅F₇N₂
• Molecular Weight: 286.15
• Product Categories: Imidazol&Benzimidazole
• Mol File: 559-37-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 226-227°C
• Boiling Point: 269.6 °C at 760 mmHg
• Flash Point: 116.8 °C
• Appearance: /
• Density: 1.559 g/cm³
• Vapor Pressure: 0.0119mmHg at 25°C
• Refractive Index: 1.472
• CAS DataBase Reference: 2-(HEPTAFLUOROPROPYL)BENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(HEPTAFLUOROPROPYL)BENZIMIDAZOLE(559-37-5)
• EPA Substance Registry System: 2-(HEPTAFLUOROPROPYL)BENZIMIDAZOLE(559-37-5)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 559-37-5(Hazardous Substances Data)

Usage

General Description

2-(Heptafluoropropyl)benzimidazole is a chemical compound with the molecular formula C10H4F7N2. It is a benzimidazole derivative that contains a heptafluoropropyl group attached to the benzene ring. This chemical is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals due to its unique fluorinated structure. It has also been studied for its potential applications in materials science, such as in the development of fluorinated polymers and coatings. Additionally, 2-(heptafluoropropyl)benzimidazole has shown promise as a potential corrosion inhibitor due to its ability to form a protective film on metal surfaces.

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 
• 115479-06-6 2-Acetyl-4,4,5,5,6,6,6-heptafluoro-3-oxo-hexanoic acid ethyl ester 
• 74728-99-7 trans/cis-dodecafluoro-3,4-epoxyhexane 
• 3709-90-8 1,2-epoxy-1,1,2,3,3,4,4,4-octafluorobutane 

Relevant articles and documents

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

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.

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.