4-nitro-1H-1,2,3-benzotriazole

Base Information

• Chemical Name: 4-nitro-1H-1,2,3-benzotriazole
• CAS No.: 6299-39-4
• Molecular Formula: C6H4N4O2
• Molecular Weight: 164.123
• Hs Code.: 2933990090
• European Community (EC) Number: 228-579-7
• NSC Number: 44657
• UNII: S75GE4B24J
• DSSTox Substance ID: DTXSID70212198
• Nikkaji Number: J206.871K
• Wikidata: Q83087248
• ChEMBL ID: CHEMBL1456115
• Mol file: 6299-39-4.mol

Synonyms:4-nitrobenzotriazole

Chemical Property of 4-nitro-1H-1,2,3-benzotriazole

Chemical Property:

• Vapor Pressure: 2.25E-06mmHg at 25°C
• Melting Point: 163-173 °C
• Refractive Index: 1.761
• Boiling Point: 392.7 °C at 760 mmHg
• PKA: 6.13±0.40(Predicted)
• Flash Point: 191.3 °C
• PSA: 87.39000
• Density: 1.638 g/cm³
• LogP: 1.38930
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 164.03342538
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

99.9% ^*data from raw suppliers

4-Nitro-1H-1,2,3-benzotriazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=NNN=C2C(=C1)[N+](=O)[O-]
• General Description: **4-Nitro-1H-1,2,3-benzotriazole** is a nitro-substituted benzotriazole derivative used as an intermediate in the synthesis of triazoloquinolone compounds with anti-mycobacterial properties. In this context, it undergoes alkylation with benzyl bromide to form benzyl benzotriazoles, which are further functionalized into quinolone derivatives. These derivatives demonstrate selective activity against *Mycobacterium tuberculosis*, including drug-resistant strains, while exhibiting low cytotoxicity. 4-NITRO-1H-1,2,3-BENZOTRIAZOLE itself serves as a key building block in the development of narrow-spectrum anti-tuberculosis agents.

Technology Process of 4-nitro-1H-1,2,3-benzotriazole

There total 11 articles about 4-nitro-1H-1,2,3-benzotriazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.7%

1,2,3-Benzotriazole (95-14-7,27556-51-0) → 4-nitro-1H-benzotriazole (6299-39-4)

Guidance literature:

With sulfuric acid; nitric acid; at 30 - 60 ℃;

DOI:10.1002/mrc.2366

Reference yield: 88.0%

2,3-diamino-nitrobenzene (3694-52-8) → 4-nitro-1H-benzotriazole (6299-39-4)

Guidance literature:

With acetic acid; In water; at 70 - 80 ℃; for 0.5h;

DOI:10.1080/00397911.2012.744840

Reference yield: 87.0%

1,2,3-Benzotriazole (95-14-7,27556-51-0) → 7-nitro-1H-benzo[d][1,2,3]triazole (6299-39-4)

Guidance literature:

With sulfuric acid; potassium nitrate; at 0 - 60 ℃; for 3.5h;

DOI:10.1016/j.tetlet.2006.04.079

upstream raw materials:

1,2,3-Benzotriazole

cyclopentyl nitrite

2,3-diamino-nitrobenzene

2,6-dinitroaniline

Downstream raw materials:

4-iodo-1H-benzotriazole

1H-1,2,3-benzotriazol-4-amine

7-amino-1H-benzotriazol-4-ol

4,5,6,7-tetrachloro-1H-benzotriazole

Refernces

Synthesis and anti-mycobacterial activities of triazoloquinolones

10.1016/j.ejmech.2010.11.020

The research focuses on the synthesis and anti-mycobacterial activities of triazoloquinolones, a class of quinolone derivatives with potential as anti-tuberculosis agents. The study confirms that these compounds exhibit selective anti-mycobacterial activity without cytotoxicity. The synthetic route involved the alkylation of 4-nitrobenzotriazole with benzyl bromide to form benzyl benzotriazoles, which were then reduced and reacted to form quinolone derivatives. The synthesized compounds were evaluated for their activity against Mycobacterium tuberculosis, including multi-drug resistant strains, as well as a range of Gram-positive and Gram-negative bacteria and Candida species. The most promising compounds were also tested for cytotoxicity in human hematological tumor cell cultures. The results showed that specific triazoloquinolones had potent anti-mycobacterial activity comparable to reference drugs, with a narrow spectrum of activity and favorable cytotoxicity profiles. The research utilized various analytical techniques, including NMR spectroscopy and mass spectrometry, to characterize the synthesized compounds.

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