272-97-9

Basic information

• Product Name: 5-AZABENZIMIDAZOLE
• Synonyms: 5-AZABENZIMIDAZOLE;1H-Imidazo(4,5-c)pyridine;3,5-Diazaindole;5-Aza-1H-benzoimidazole;5-AzabenziMidazole 97%
• CAS NO: 272-97-9
• Molecular Formula: C₆H₅N₃
• Molecular Weight: 119.12
• Product Categories: Benzimidazoles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 272-97-9.mol
• Article Data: 27

Chemical Properties

• Melting Point: 168-172 °C(lit.)
• Boiling Point: 425.1°Cat760mmHg
• Flash Point: 224.4°C
• Appearance: Beige/Powder
• Density: 1.348
• Vapor Pressure: 4.85E-07mmHg at 25°C
• Refractive Index: 1.715
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.15±0.30(Predicted)
• BRN: 2601
• CAS DataBase Reference: 5-AZABENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AZABENZIMIDAZOLE(272-97-9)
• EPA Substance Registry System: 5-AZABENZIMIDAZOLE(272-97-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 272-97-9(Hazardous Substances Data)

Usage

Description

5-AZABENZIMIDAZOLE is an organic compound with the molecular formula C7H6N4. It is a derivative of benzimidazole, featuring a nitrogen atom at the fifth position. 5-AZABENZIMIDAZOLE is known for its unique chemical properties and potential applications in various fields.

Uses

Used in Chemical Synthesis:
5-AZABENZIMIDAZOLE is used as a chemical intermediate for the synthesis of various compounds, particularly those involving the benzimidazole core structure. Its presence in the molecule can significantly alter the properties and reactivity of the final product.
Used in Zeolitic Imidazolate Frameworks (ZIF) Production:
5-AZABENZIMIDAZOLE is used as a building block for the preparation of ZIF-22 membranes. These membranes are part of a class of materials known as Zeolitic Imidazolate Frameworks, which have a wide range of applications due to their unique properties, such as high porosity, tunable pore sizes, and exceptional chemical stability.
ZIF-22, in particular, is a subtype of ZIF materials that has gained attention for its potential use in various applications, including gas separation, catalysis, and energy storage. The incorporation of 5-AZABENZIMIDAZOLE in the synthesis of ZIF-22 membranes contributes to the development of advanced materials with tailored properties for specific industrial needs.

InChI:InChI=1/C6H5N3/c1-2-7-3-6-5(1)8-4-9-6/h1-4H,(H,8,9)

Upstream product

• 3243-24-1 imidazo<4,5-c>pyridine-4-one 
• 54-96-6 3,4-diaminopyridine 
• 149-73-5 trimethyl orthoformate 
• 617-84-5 N-formyldiethylamine 
• 68-12-2 N,N-dimethyl-formamide 
• 124-38-9 carbon dioxide 
• 122-51-0 orthoformic acid triethyl ester 
• 3724-43-4 Vilsmeier reagent 
• 14036-06-7 diethoxymethyl acetate 
• 1758-73-2 Aminoiminomethanesulfinic acid 
• 1681-37-4 4-amino-3-nitropyridine 
• 89792-18-7 3,4-bis(formylamino)pyridine 
• 33631-02-6 3,4-diamino-pyridin-2-ol 
• 105952-93-0 5-aminoimidazo<4,5-c>pyridinium mesitylenesulfonate 

Downstream Products

• 91184-02-0 1H-Imidazo[4,5-c]pyridine-N-oxide 
• 179022-71-0 1-[2-[4-(phenylmethyl)phenoxy]ethyl]-1H-imidazo[4,5-c]pyridine 
• 179021-34-2 3-[2-[4-(phenylmethyl)phenoxy]ethyl]-3H-imidazo[4,5-c]pyridine 
• 179066-52-5 2,6-bis(1,1-dimethylethyl)-4-[[3-(5H-imidazo-[4,5-c]pyridin-5-yl)propyl]thio]phenol 
• 863675-61-0 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine 
• 78582-15-7 4-chloro-1-(2'-deoxy-β-D-erythro-pentofuranosyl)-1H-imidazo<4,5-c>pyridine 
• 78582-17-9 4-Amino-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-imidazo<4,5-c>pyridine 
• 6811-77-4 3-deazaadenine 

Relevant articles and documents

Impact of 3-deazapurine nucleobases on RNA properties

Deazapurine nucleosides such as 3-deazaadenosine (c3A) are crucial for atomic mutagenesis studies of functional RNAs. They were the key for our current mechanistic understanding of ribosomal peptide bond formation and of phosphodiester cleavage in recentl

In Situ Formation of Frustrated Lewis Pairs in a Water-Tolerant Metal-Organic Framework for the Transformation of CO2

Frustrated Lewis pairs (FLPs) consist of sterically hindered Lewis acids and Lewis bases, which provide high catalytic activity towards non-metal-mediated activation of “inert” small molecules, including CO2 among others. One critical issue of homogeneous FLPs, however, is their instability upon recycling, leading to catalytic deactivation. Herein, we provide a solution to this issue by incorporating a bulky Lewis acid-functionalized ligand into a water-tolerant metal-organic framework (MOF), named SION-105, and employing Lewis basic diamine substrates for the in situ formation of FLPs within the MOF. Using CO2 as a C1-feedstock, this combination allows for the efficient transformation of a variety of diamine substrates into benzimidazoles. SION-105 can be easily recycled by washing with MeOH and reused multiple times without losing its identity and catalytic activity, highlighting the advantage of the MOF approach in FLP chemistry.

Synthesis of 1H-1,3-benzimidazoles, benzothiazoles and 3H-imidazo[4,5-c]pyridine using DMF in the presence of HMDS as a reagent under the transition-metal-free condition

An operationally simple method for synthesis of benzimidazole and 3H-imidazo[4,5-c]pyridine from o-phenylenediamine or pyridine-3, 4-diamine and N,N-dimethylformamide (DMF) in the presence of hexamethyldisilazane (HMDS) as a reagent is described. To evaluate the scope of application of this reagent, it was also used to prepare benzothiazole, 1H-perimidine, and benzoxazole, which was successful for benzothiazole and 1H-perimidine but benzoxazole was not formed. This reaction complies with the principles of green chemistry as it does not use toxic solvents, transition metals, or strong acids. The products are obtained in moderate to excellent yields.