108413-26-9

Basic information

• Product Name: 1H-Benzimidazole,1-(3-butenyl)-(9CI)
• Synonyms: 1H-Benzimidazole,1-(3-butenyl)-(9CI)
• CAS NO: 108413-26-9
• Molecular Formula: C₁₁H₁₂N₂
• Molecular Weight: 172.22638
• Product Categories: BENZIMIDAZOLE
• Mol File: 108413-26-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Benzimidazole,1-(3-butenyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole,1-(3-butenyl)-(9CI)(108413-26-9)
• EPA Substance Registry System: 1H-Benzimidazole,1-(3-butenyl)-(9CI)(108413-26-9)

Safety Data

• Hazardous Substances Data: 108413-26-9(Hazardous Substances Data)

Upstream product

• 51-17-2 benzoimidazole 
• 5162-44-7 1-bromo-4-butene 
• 40671-34-9 4-methanesulfonyloxy-1-butene 

Downstream Products

• 16405-81-5 1-(but-2-en-1-yl)-1H-benzo[d]imidazole 
• 16405-81-5 1-crotylbenzimidazole 
• 5622-83-3 1,2,3,4-tetrahydro-pyrido[1,2-a]benzimidazole 
• 29981-98-4 3-methyl-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole 

Relevant articles and documents

Construction of All-Carbon Quaternary Stereocenters by Scandium-Catalyzed Intramolecular C-H Alkylation of Imidazoles with 1,1-Disubstituted Alkenes

The exo-selective C-H cycloaddition of imidazoles to 1,1-disubstituted alkenes has been achieved for the first time by using half-sandwich scandium catalysts. A wide range of imidazole compounds bearing various 1,1-disubstituted aliphatic alkenes, styrenes, dienes, and enynes have been selectively converted in high yields to the corresponding bicyclic imidazole derivatives bearing β-all-carbon-substituted quaternary stereocenters. By using a chiral half-sandwich scandium catalyst, the asymmetric exo-selective cyclization has also been achieved with a high level of enantioselectivity.

Axially chiral macrocyclic E-alkene bearing bisazole component formed by sequential C-H homocoupling and ring-closing metathesis

Clipping by ring-closing metathesis freezes rotation of a C-C bond to result in forming axial chirality. Treatment of bisbenzimidazole bearing an N-(3-butenyl) substituent with a Grubbs' catalyst undergoes ring-closing metathesis, in which the stereochemistry of the thus formed olefin was exclusively E-form. Analysis by HPLC with a chiral stationary column confirmed clear baseline separation of each enantiomer.

Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazolesviaa sulfinyl radical

A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to a broad range of benzimidazole and deuterated benzimidazole products in generally high yields with good tolerance of various synthetically and pharmaceutically useful functionalities. The mechanistic studies reveal that both single electron transfer and energy transfer probably occur in the initial step and a sulfinyl radical intermediate is involved in the key desulfurization process.

Enantioselective Ni-Al Bimetallic Catalyzed exo -Selective C-H Cyclization of Imidazoles with Alkenes

A Ni-Al bimetallic catalyzed enantioselective C-H exo-selective cyclization of imidazoles with alkenes has been developed. A series of bi- or polycyclic imidazoles with β-stereocenter were obtained in up to 98% yield and >99% ee. The bifunctional SPO ligand-promoted bimetallic catalysis proved to be critical to this challenging stereocontrol.

Benzimidazole-derived ATP analogues as potential glutamine synthetase inhibitors

A series of mono-and dihydroxyalkyl-and-alkyloxybenzimidazoles and their phosphorylated derivatives have been prepared as adenosine triphoshate analogues for investigation as potential M. Tb. glutamine synthetase inhibitors. Taylor & Francis Group, LLC.

Microwave-assisted C-H bond activation: A rapid entry into functionalized heterocycles

(Matrix presented) Microwave irradiation strongly accelerates the rhodium-catalyzed intramolecular coupling of a benzimidazole C-H bond to pendant alkenes. The cyclic products were formed in moderate to excellent yields with reaction times less than 20 min. Additionally, the use of microwave irradiation allowed the reactions to be performed without any solvent purification and with minimal precautions to exclude air.

Tin-free radical sequences under acidic conditions. Convergent access to azole-containing structures

(equation presented) Various xanthates add efficiently to olefins bearing [1,2,4]triazole, imidazole, or benzimidazole moieties in the presence of camphorsulfonic acid via a radical chain reaction initiated by a small amount of lauroyl peroxide. The adducts may be transformed to more complex molecules by implementing a further radical cyclization.

3-Imidazolium cephalosporin derivatives

A cephalosporin compound substituted by imidazolium ring in 3-position of cephem having the following formula (I), and pharmaceutically acceptable salt thereof, STR1 wherein R1 is an organic residue known in β-lactam antibiotics, R2 is hydrogen atom or methoxy, n is 0 or 1, A is a nitrogen-containing group constituting imidazolium ring, is useful as an agent for preventing and treating bacterial infections.