1516-73-0

Basic information

• Product Name: 2-AZIDO-1-METHYLBENZIMIDAZOLE
• Synonyms: 2-AZIDO-1-METHYLBENZIMIDAZOLE
• CAS NO: 1516-73-0
• Molecular Formula: C₈H₇N₅
• Molecular Weight: 0
• Mol File: 1516-73-0.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 2-AZIDO-1-METHYLBENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AZIDO-1-METHYLBENZIMIDAZOLE(1516-73-0)
• EPA Substance Registry System: 2-AZIDO-1-METHYLBENZIMIDAZOLE(1516-73-0)

Safety Data

• Hazardous Substances Data: 1516-73-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H7N5/c1-13-7-5-3-2-4-6(7)10-8(13)11-12-9/h2-5H,1H3

Upstream product

• 1632-83-3 1-Methylbenzimidazole 
• 1849-02-1 2-chloro-1-methyl-benzimidazole 
• 7022-37-9 1-methyl-2-hydrazinobenzimidazole 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 49572-60-3 2-bromo-1-methyl-1H-benzo[d]imidazole 

Downstream Products

• 76944-95-1 tert-butyl N-[(3S)-2-oxoazepan-3-yl]carbamate 
• 1622-57-7 2-Amino-1-methylbenzimidazole 

Relevant articles and documents

Iron-Mediated Electrophilic Amination of Organozinc Halides using Organic Azides

A wide range of alkyl-, aryl- and heteroarylzinc halides were aminated with highly functionalized alkyl, aryl, and heterocyclic azides. The reaction proceeds smoothly at 50 °C within 1 h in the presence of FeCl3 (0.5 equiv) to furnish the corresponding secondary amines in good yields. This method was extended to peptidic azides and provided the arylated substrates with full retention of configuration. To demonstrate the utility of this reaction, we prepared two amine derivatives of pharmaceutical relevance using this iron-mediated electrophilic amination as the key step.

Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation

Arene amination is achieved by site-selective C-H zincation followed by copper-catalyzed coupling with O-benzoylhydroxylamines under mild conditions. Key to this success is ortho-zincation mediated by lithium amidodiethylzincate base that is effective for a wide range of arenes, including nonactivated arenes bearing simple functionalities such as fluoride, chloride, ester, amide, ether, nitrile, and trifluoromethyl groups as well as heteroarenes including indole, thiophene, pyridine, and isoquinoline. An analogous C-H azidation is also accomplished using azidoiodinane for direct introduction of a useful azide group onto a broad scope of arenes and heteroarenes. These new transformations offer rapid access to valuable and diverse chemical space of aminoarenes. Their broad applications in organic synthesis and drug discovery are demonstrated in the synthesis of novel analogues of natural product (-)-nicotine and antidepressant sertraline by late-stage amination and azidation reactions.

Water compatible photoarylation of amino acids and peptides

A novel photoarylation of amino acids and peptides is described, which tolerates the presence of water. Irradiation of Boc-protected amino acids in the presence of N-protected 2-azidobenzimidazoles leads to selective arylation of carboxy termini or side chains. The new reaction also works for peptides. Irradiation of the nonapeptide H-SPSYVYHQF-OH also resulted in selective arylation of the tyrosine side chains, as indicated by ESI-MS/MS fragmentation. Chemo- and regioselectivity could add the title reaction to the repertoire of photoaffinity labeling methods.

Designing Structural Motifs for Clickamers: Exploiting the 1,2,3-Triazole Moiety to Generate Conformationally Restricted Molecular Architectures

Noncovalent interactions, especially hydrogen-bonding interactions as well as electrostatic forces, confined within one macromolecule are the key to designing foldamers that adopt well-defined conformations in solution. In the context of significant recent activities in the area of triazole-connected foldamers, so-called clickamers, we present a fundamental study that compares various model compounds that bear adjacent N-, O-, or F-heteroatom substituents. The interplay of attractive and repulsive interactions leads to rotational constraints around the single bonds attached to both the 1- and 4-positions of the 1,2,3-triazole moiety and should therefore be able to induce well-defined conformational preferences in higher oligomers and polymers, that is, foldamers. Various compounds were synthesized and characterized with regard to their preferred conformations in all three aggregation statesa-that is, in the gas phase, in solution as well as in the solid statea-by employing DFT calculations, NMR spectroscopic experiments, and X-ray crystallography, respectively. On the basis of the thus-obtained general understanding of the conformational behavior of the individual connection motifs, heterostructures were prepared from different motifs without affecting their distinct folding characteristics. Therefore, this work provides a kind of foldamer construction kit, which should enable the design of various clickamers with specific shape and incorporated functionality. A foldamer construction kit: Various heterostructures "clicked" together by structure-directing triazole moieties were investigated with regard to their conformational behavior. Different heteroatoms (X; see graphic) can be used to bias the conformation around the N(1)- and C(4)-connecting single bonds of the triazoles based on tunable noncovalent interactions.

Total syntheses of naamine A and naamidine A, marine imidazole alkaloids

The first total syntheses of naamine A (4) and naamidine A (5), marine imidazole alkaloids, were achieved through twelve and thirteen steps of reactions, respectively, starting from 1-methyl-2-phenylthio-1H-imidazole (17).

Highly effective procedure for introduction of amino group into the 2-position of imidazole ring

Procedures for the preparation of 2-amino- and 2-arylaminobenzimidazoles were developed, and one of the efficient procedure was applied to the synthesis of preclathridine A, a marine imidazole alkaloid isolated from a sponge.