14209-07-5

Basic information

• Product Name: 1-Methyl-7-nitro-1H-benzotriazole
• Synonyms: 1-Methyl-7-nitro-1H-benzotriazole
• CAS NO: 14209-07-5
• Molecular Formula: C₇H₆N₄O₂
• Molecular Weight: 0
• Mol File: 14209-07-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Methyl-7-nitro-1H-benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-7-nitro-1H-benzotriazole(14209-07-5)
• EPA Substance Registry System: 1-Methyl-7-nitro-1H-benzotriazole(14209-07-5)

Safety Data

• Hazardous Substances Data: 14209-07-5(Hazardous Substances Data)

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 13183-00-1 2-amino-6-nitro-1-N-methylaniline 
• 6299-39-4 4-nitro-1H-benzotriazole 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 127280-84-6 1-Methyl-7-nitro-4-<1-(phenylsulfonyl)propyl>benzotriazol 
• 127280-83-5 1-Methyl-7-nitro-4-(phenylsulfonylmethyl)benzotriazol 
• 127280-82-4 1-Methyl-7-nitro-6-(phenylsulfonylmethyl)benzotriazol 

Relevant articles and documents

Facile alkylation of 4-nitrobenzotriazole and its platelet aggregation inhibitory activity

We explored the facile alkylation of 4-nitrobenzotriazole under basic conditions and the synthesized derivatives were tested for their potential ADP induced platelet aggregation inhibition activity in comparison with standard drug ticagrelor (selective P2Y12 inhibitor). The nitro group at 4-position is highly activating toward alkylation reactions (under strong basic conditions) and resulted in formation of degradation product like 3-nitrobenzene-1,2-diamine which make isolation of alkyl products very difficult. We optimized the reaction under mild basic condition (potassium carbonate and DMF) which is devoid of any degradation product. This is perhaps the first report of 4-nitrobenzotriazole derivatives possessing platelet aggregation inhibitory activity. Generally activity increases with increase in length of alkyl chain and 1-alkyl positional isomers were found to be more potent than 2-alkyl isomers. The benzoyl derivative was found to be the most potent [compound 22; (4-Nitro-1H-benzotriazol-1-yl)(phenyl)methanone; IC50 = 0.65 ± 0.10 mM] which may be attributed to electronegative oxygen atom and aromatic ring. Benzyl derivatives [compound 20; 1-Benzyl-4-nitro-1H-benzotriazole; IC50 = 0.81 ± 0.08 mM, compound 21; 2-Benzyl-4-nitro-2H-benzotriazole; IC50 = 0.82 ± 0.19 mM] and sulfonyl derivative [compound 23; 1-[(4-Methylphenyl)sulfonyl]-4-nitro-1H-benzotriazole; IC50 = 0.82 ± 0.19 mM] are also found to be highly active. Furthermore, all compounds possess P2Y12 binding affinity as confirmed by VASP/P2Y12 phosphorylation assay.

[1,2,3]Triazolo[4,5-h]quinolones. A new class of potent antitubercular agents against multidrug resistant Mycobacterium tuberculosis strains

In this preliminary study we report the activity of 3-methyl-9-substituted-6-oxo-6,9-dihydro-3H-[1,2,3]-triazolo[4,5-h]quinolone-carboxylic acids and their esters as a new class of antiinfective agents against MDR Mycobacterium tuberculosis. In antitubercular screening against H37Rv and 11 clinically isolated strains of M. tuberculosis several derivatives (1o,3a,c,i,j,p) showed MIC90 in the range 0.5-3.2 μg/mL. 3c showed no cytotoxicity and proved to be the most potent derivative exhibiting MIC90 = 0.5 μg/mL against all M. tuberculosis strains and infected human macrophages (J774-A1) tested.