6299-39-4

Basic information

• Product Name: 4-NITRO-1H-1,2,3-BENZOTRIAZOLE
• Synonyms: 4-NITRO-1H-1,2,3-BENZOTRIAZOLE;4-NITRO-1H-BENZOTRIAZOLE;Nitro-1H-benzotriazole;7-Nitro-1H-benzotriazole;4-nitro-2H-benzotriazole;1H-Benzotriazole, 4-nitro-;4-nitro-1H-benzo[d][1,2,3]triazole;Benzotriazole, 4-nitro-
• CAS NO: 6299-39-4
• Molecular Formula: C₆H₄N₄O₂
• Molecular Weight: 164.12
• EINECS: 228-579-7
• Mol File: 6299-39-4.mol
• Article Data: 23

Chemical Properties

• Melting Point: 163-173 °C
• Boiling Point: 392.7 °C at 760 mmHg
• Flash Point: 191.3 °C
• Appearance: /
• Density: 1.638 g/cm³
• Vapor Pressure: 2.25E-06mmHg at 25°C
• Refractive Index: 1.761
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 6.13±0.40(Predicted)
• CAS DataBase Reference: 4-NITRO-1H-1,2,3-BENZOTRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITRO-1H-1,2,3-BENZOTRIAZOLE(6299-39-4)
• EPA Substance Registry System: 4-NITRO-1H-1,2,3-BENZOTRIAZOLE(6299-39-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 6299-39-4(Hazardous Substances Data)

Usage

General Description

4-NITRO-1H-1,2,3-BENZOTRIAZOLE is a chemical compound that belongs to the family of benzotriazoles. It is a yellow crystalline powder that is insoluble in water and organic solvents. 4-NITRO-1H-1,2,3-BENZOTRIAZOLE is primarily used as a corrosion inhibitor in industrial fluids, such as coolants and metalworking fluids. It is also used as a stabilizer for plastics and rubber, as well as in the production of dyes and pigments. 4-NITRO-1H-1,2,3-BENZOTRIAZOLE is known to be toxic and may cause irritation to the skin, eyes, and respiratory system upon exposure. Therefore, proper safety precautions must be taken when handling and using this chemical.

InChI:InChI=1/C6H4N4O2/c11-10(12)5-3-1-2-4-6(5)8-9-7-4/h1-3H,(H,7,8,9)

Upstream product

• 67764-33-4 cyclopentyl nitrite 
• 3694-52-8 2,3-diamino-nitrobenzene 
• 95-14-7 1,2,3-Benzotriazole 
• 606-21-3 1-chloro-2,6-dinitrobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 606-22-4 2,6-dinitroaniline 

Downstream Products

• 127280-73-3 4-Nitro-7-(phenylsulfonylmethyl)benzotriazol 
• 127280-91-5 5-Benzenesulfonylmethyl-4-nitro-1H-benzotriazole 
• 127280-74-4 4-Nitro-7-<1-(phenylsulfonyl)propyl>benzotriazol 
• 144072-72-0 C₃₂H₂₁Cl₃N₄O₉ 
• 144072-61-7 4-nitro-1-<2,3,5-tris-O-(p-chlorobenzoyl)-β-D-ribofuranosyl>benzotriazole 
• 14209-07-5 1-methyl-7-nitro-1H-benzotriazole 
• 89795-90-4 2-methyl-4-nitro-2H-benzotriazole 
• 27799-86-6 1-methyl-4-nitro-1H-benzotriazole 
• 1265890-81-0 1-benzyl-7-nitrobenzotriazole 
• 66382-08-9 1-benzyl-4-nitro-1H-benzotriazole 
• 66382-17-0 2-benzyl-4-nitro-2H-benzotriazole 
• 1395320-45-2 1-ethyl-7-nitro-4-[1-(phenylsulfonyl)propyl]-1H-benzotriazole 
• 1395320-43-0 2-ethyl-4-nitro-7-[1-(phenylsulfonyl)propyl]-2H-benzotriazole 
• 1395320-39-4 1-ethyl-4-nitro-7-[1-(phenylsulfonyl)propyl]-1H-benzotriazole 

Relevant articles and documents

CYCLIC DINUCLEOTIDES AS ANTICANCER AGENTS

The present invention is directed to compounds of the formula (I) wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

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.

INDAZOLE DERIVATIVES AS ADENOSINE MONOPHOSPHATE DEAMINASE (AMPD) INHIBITORS FOR USE IN DIABETES AND RELATED DISEASES OF METABOLIC SYNDROME

Herein, we describe a method for treatment of diabetes and other disorders classified as Metabolic Syndrome. The invention provides novel AMP Deaminase (AMPD) inhibitors comprising novel indazole and benzotriazole derivatives including a phosphorous containing derivative, a carboxylic acid, or an amino acid ester prodrug. The invention also provides support for a novel mechanism of action for the existing drug metformin: direct inhibition of the enzyme AMPD. The inhibition of AMPD in turn activates AMP Kinase, known to be linked to the action of metformin. The invention also makes novel use of a double inhibitor assay allowing identification of selective AMPD inhibitors over ADA inhibitors. The new inhibitors, structurally distinct from metformin, offer selectivity that may obviate side effects known for metformin itself, providing new benefits for diabetes and Metabolic Syndrome.