26334-20-3

Basic information

• Product Name: 1,3-Dimethyl-2-azidobenzene
• Synonyms: 2-Azido-1,3-dimethylbenzene;1,3-Dimethyl-2-azidobenzene
• CAS NO: 26334-20-3
• Molecular Formula: C₈H₉N₃
• Molecular Weight: 0
• Mol File: 26334-20-3.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Dimethyl-2-azidobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethyl-2-azidobenzene(26334-20-3)
• EPA Substance Registry System: 1,3-Dimethyl-2-azidobenzene(26334-20-3)

Safety Data

• Hazardous Substances Data: 26334-20-3(Hazardous Substances Data)

Usage

Class

Azobenzenes (aromatic compounds containing a central azo group, a nitrogen-nitrogen double bond, and two aryl groups)

Physical state

Colorless liquid at room temperature

Molecular weight

159.19 g/mol

Uses

a. Organic synthesis
b. Chemical research
c. Building block for creating various derivatives and functionalized molecules
d. Precursor for synthesizing polymers and materials with specific properties

Safety precautions

Handle with care due to potential explosive and toxic nature of azides

InChI:InChI=1/C8H9N3/c1-6-4-3-5-7(2)8(6)10-11-9/h3-5H,1-2H3

Upstream product

• 87-62-7 2,6-dimethylaniline 
• 100379-00-8 2,6-dimethylbenzene boronic acid 
• 81-20-9 2,6-dimethylnitrobenzene 

Downstream Products

• 128654-40-0 9-(2,6-dimethylphenyl)-9-azabicyclo<6.1.0>nonane 
• 120578-20-3 4-amino-3,5-dimethylphenyl methyl sulphide 
• 87-62-7 2,6-dimethylaniline 
• 128654-39-7 8-(2,6-dimethylphenyl)-8-azabicyclo<5.1.0>octane 
• 96249-39-7 2,6-dimethylphenylnitrene 
• 85526-27-8 N-(2,6-Dimethylphenyl)triphenylphosphanimid 
• 54810-82-1 3,5-dimethyl-[1,1'-biphenyl]-4-amine 
• 28556-81-2 2,6-dimethylphenylisocyanate 
• 172094-23-4 2-azido-1,3-bis(bromomethyl)benzene 
• 609769-99-5 2-(2,6-Me₂C₆H₃NPPh₂)C₅H₄N 
• 1026886-34-9 1-azido-2,6-bis(trideuteriomethoxymethyl)benzene 
• 85526-35-8 N-(2,6-Dimethylphenyl)-2-phenyl-2-(phenylsulfonyl)ethenimin 
• 85526-45-0 N-(2,6-Dimethylphenyl)-1-(2,6-dimethylphenylimino)-3-(phenylsulfonyl)-1H-inden-2-amin 
• 85526-37-0 2',4'-Bis(2,6-dimethylphenylimino)spirophenanthro<9,10-b>pyran>-10-on 

Relevant articles and documents

Design, synthesis and photoluminescent studies of new 1,5-benzodiazepines derivatives: Towards new ESIPT compounds

A series of novel N1-triazolo-4-(2-hydroxyphenyl)-1,5-benzodiazepin-2-ones 7a-e and N5-triazolo-4-(2-acetoxyphenyl)-1,5-benzodiazepin-2-ones 8a-e were designed and synthesized in good yields via a Cu(I) catalyzed 1,3-dipolar alkyne-azide coupling reaction (CuAAC) between the N1- and N5-propargyl-1,5-benzodiazepines 2 and 5 respectively and various arylazides 6a-e. Photophysical properties were investigated for all the obtained triazolo-benzodiazepine hybrids by mean of absorption and fluorescence spectral techniques. Thus, a fluorescent emission was detected for the derivatives 7a-e in aggregated state. On another hand, the O-acetylated derivatives 8a-e were found to be not emissive. Finally, we have chosen a model reaction to demonstrate that upon deprotecting the -OAc group in the N1, N5-disubstituted benzodiazepine 8d a moderate fluorescence reappeared in the obtained product 9d proving that an ESIPT process can take place as long as the hydroxyl group remains free, allowing the OH/C[dbnd]O proton transfer to occur. A computational study of compounds 7e and 9d in vacuo provide further details and arguments to rationalize the fluorescence of these compounds in aqueous mixtures.

Synthesis and Biological Evaluation of New Ibuprofen-1,3,4-oxadiazole-1,2,3-triazole Hybrids

A new hybrid polydentate template comprising distinctive pharmacophoric groups, namely, ibuprofen, 1,3,4-oxadiazole, and 1,2,3-triazole linked through a thioether bridge was achieved by one-pot synthesis by exploring multicomponent Cu-catalyzed “click chemistry” approach. The target structures were characterized by NMR, IR, and LC-Mass. The X-ray analysis of 2-(1-(4-isobutylphenyl)ethyl)-5-(((1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-1,3,4-oxadiazole (8a) confirmed the assigned structure. The in vitro antibacterial and anticancer activity of these compounds revealed that 2-(1-(4-isobutylphenyl)ethyl)-5-(((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)thio)-1,3,4-oxadiazole (8b) demonstrated more potent antibacterial activity against Gram-negative strains (Escherichia coli and Pseudomonas aeruginosa) and 2-(((1-(2,4-dimethylphenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-5-(1-(4 isobutylphenyl)ethyl)-1,3,4-oxadiazole (8e) exhibited anticancer activity with IC50 of 27.50 and 31.03?μg/mL against HeLa and MCF-7 cell lines, respectively.

Ruthenium Bisammine Complex and Its Reaction with Aryl Azides

A ruthenium bisammine complex was formed in the reaction of ruthenium 1,4-dibenzyltetraazadiene complex with primary amines at room temperature, which was a versatile precursor for the synthesis of various Ru(II) complexes through ligand exchange reactions. In the reaction with azidobenzene, ruthenium 1,4-diphenyltetraaza-1,3-diene complex was formed, while ruthenium imido complexes were given in the reaction with bulky aryl azides such as 2-azido-1,3-dimethylbenzene and 2-azido-1,3-diisopropylbenzene. The ruthenium imido complexes showed high catalytic activity in the reaction of alkyl azides with primary amines to afford N-substituted imines.