14984-26-0

Basic information

• Product Name: 1H-Benzimidazole,2-ethenyl-(9CI)
• Synonyms: 1H-Benzimidazole,2-ethenyl-(9CI);2-VINYL-1H-BENZIMIDAZOLE;2-ethenyl-1H-benzimidazole
• CAS NO: 14984-26-0
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.18
• Product Categories: BENZIMIDAZOLE;Imidazol&Benzimidazole
• Mol File: 14984-26-0.mol

Chemical Properties

• Boiling Point: 322.7 °C at 760 mmHg
• Flash Point: 166.2 °C
• Appearance: /
• Density: 1.191 g/cm³
• Vapor Pressure: 0.000274mmHg at 25°C
• Refractive Index: 1.714
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 1H-Benzimidazole,2-ethenyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole,2-ethenyl-(9CI)(14984-26-0)
• EPA Substance Registry System: 1H-Benzimidazole,2-ethenyl-(9CI)(14984-26-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 14984-26-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 63, p. 7077, 2007 DOI: 10.1016/j.tet.2007.05.010

InChI:InChI=1/C9H8N2/c1-2-9-10-7-5-3-4-6-8(7)11-9/h2-6H,1H2,(H,10,11)

Upstream product

• 50-00-0 formaldehyd 
• 60912-44-9 ((1H-benzo[d]imidazol-2-yl)methyl)triphenylphosphonium chloride 
• 16414-04-3 1-benzimidazol-2-ylethanol 
• 136642-47-2 1-<2-(1H-benzimidazol-2-yl)ethyl>pyridinium tetrafluoroborate 
• 138972-85-7 2-vinylbenzimidazole N-oxide 
• 13347-27-8 N-(2-Nitrophenyl)-N-prop-2-enylamine 
• 609-73-4 o-nitroiodobenzene 
• 107616-24-0 N-(2-nitrophenyl)-N-(2-propenyl)acetamide 
• 88-74-4 2-nitro-aniline 
• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 590-92-1 3-Bromopropionic acid 
• 95-54-5 1,2-diamino-benzene 
• 79-06-1 2-propenamide 

Downstream Products

• 1428555-72-9 1-benzyl-2-ethenyl-1H-benzimidazole 

Relevant articles and documents

Palladium-catalyzed tandem one-pot synthesis of π-expanded imidazoles through a sequential Heck and oxidative amination reaction

An efficient palladium-catalyzed route for tandem synthesis of imidazole-fused polyheterocycles from 2-vinyl imidazoles and aryl halides is described. The sequentially accomplished process comprises intermolecular Heck arylation of 2-vinyl imidazoles followed by an intramolecular aerobic oxidative C-H amination reaction promoted by the same Pd catalyst. This Pd-catalyzed tandem approach offers a straightforward protocol for the assembly of benzimidazo/phenanthroimidazo[1,2-a]quinolines in moderate to high yields, serving as a useful tool for the discovery of fluorescent materials.

Expedient synthesis of benzimidazoles using amides

In the present report an efficient, rapid, facile and inexpensive route for the synthesis of benzimidazoles using 1,2-arylenediamines and N,N-dimethylformamide in acidic medium under thermal/microwave condition is developed. This reaction was further explored with the different amides to afford a library of 2-substituted benzimidazoles. The advantage of the present synthetic method includes shorter reaction time, easy work up and excellent yields without using catalysts.

A new route to pyrimido[1,6-a]benzimidazole derivatives

(Chemical Equation Presented) Cyclocondensation of orthophenylendiamines with 3-bromopropionic acid in PPA afforded 2-vinyl-benzimidazoles which were subsequently converted to their corresponding 2-(1,2-dibromoethyl)-1H- benzimidazoles on treatment with bromine. Reaction of these compounds with aryl nitriles or aryl isocyanates in basic chloroform yielded 1-arylpyrimido[1,6-a] benzimidazoles and 2-arylpyrimido[1,6-a]-benzimidazol-3-ones respectively.

Palladium-catalyzed N-heteroannulation of N-allyl- or N-benzyl-2-nitrobenzenamines: synthesis of 2-substituted benzimidazoles

A palladium-catalyzed reductive N-heteroannulation of N-allyl- or N-benzyl-2-nitrobenzenamines, using carbon monoxide as the ultimate reducing agent, affording 2-substituted benzimidazoles has been developed.

Synthesis of dipolar ethyleneimidazolium benzimidazolate inner salts and their transformation to 2-vinylbenzimidazoles through A type of β-elimination reaction

The synthesis and spectroscopic properties of the fairly stable title inner salts (5) are reported. For several of the betaines (5), both the highly dipolar character due to the terminal rings and the nature of the spacer promoted a type of β-elimination reaction. Thus, formation of 2-vinylbenzimidazoles (7) from the corresponding betaines (5) proceeds in high yield under neutral and mild conditions. Following similar treatment, the 1-(2-benzimidazol-2-ylethyl)imidazolium salt (8b) undergo nucleophilic substitution reactions.

CONVERSIONS OF 2-α-CHLOROALKYLBENZIMIDAZOLES

Upon interaction with caustic in a DMSO medium, 2-chloromethylbenzimidazoles are subjected to cyclodimerization, forming 5H,12H-pyrazinobis-benzimidazoles; in the presence of nucleophiles (ammonia, amines, anions of β-diketones), under the indicated conditions, the products are the corresponding substituted amines or derivatives of pyrrolobenzimidazole.

Heterocyclic Betaines. Novel Ethyleneimidazolium Benzimidazolate Inner Salts. Synthesis, Characterization, and Transformation into 2-Vinyl-1H-benzimidazoles

The first synthesis of the hitherto unknown ethyleneimidazolium benzimidazolate inner salts is described.Their dipolar structure is well reflected on the basis of the 1H and 13C NMR parameters.Under neutral and mild conditions the title compounds underwent a type of β-elimination, affording their corresponding 2-vinyl-1H-benzimidazoles in high yields.

An Efficient Synthesis of 2-Vinylbenzimidazoles from 1-(2-Benzimidazole-2-ylethyl)pyridinium Salts Using an Anion-Exchange Resin

Transformation of several 1-(2-benzimidazol-2-ylethyl)pyridinium salts, obtained by two different procedures, into their corresponding 2-vinylbenzimidazoles either using an anion-exchange resin (OH- form) or in the solid state is described.This approach now allows a facile entry into the almost unknown 2-vinylbenzimidazole monomers.