7570-47-0

Basic information

• Product Name: 2-METHYL-5-NITROINDOLE
• Synonyms: LABOTEST-BB LT00441288;AKOS BBS-00002627;5-NITRO-2-METHYLINDOLE;2-METHYL-5-NITROINDOLE;2-METHYL-5-NITRO-1H-INDOLE;2-Methyl-5-nitroindole,95%;2-Methyl-5-nitroindole, 95% 2.5GR;NSC 131898
• CAS NO: 7570-47-0
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 7570-47-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: 172-176 °C(lit.)
• Boiling Point: 307.77°C (rough estimate)
• Flash Point: 174.9 °C
• Appearance: Yellow to orange-brown/Crystalline Powder
• Density: 1.2662 (rough estimate)
• Vapor Pressure: 3.27E-05mmHg at 25°C
• Refractive Index: 1.5570 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-METHYL-5-NITROINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-5-NITROINDOLE(7570-47-0)
• EPA Substance Registry System: 2-METHYL-5-NITROINDOLE(7570-47-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 7570-47-0(Hazardous Substances Data)

Usage

Description

2-METHYL-5-NITROINDOLE is an organic compound with the molecular formula C9H8N2O2. It is a derivative of indole, featuring a methyl group at the 2nd position and a nitro group at the 5th position. 2-METHYL-5-NITROINDOLE is known for its potential applications in various chemical and pharmaceutical processes due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
2-METHYL-5-NITROINDOLE is used as a reactant for the preparation of various pharmaceutical compounds, including:
1. βCyanoindoles: These compounds are utilized as building blocks in the synthesis of various biologically active molecules.
2. Methanoindoles: These are important intermediates in the development of drugs targeting specific receptors or enzymes.
3. Protein kinase C theta (PKCθ) inhibitors: PKCθ is a critical enzyme involved in various cellular processes, and its inhibition can have therapeutic benefits in treating certain diseases.
4. Tubulin polymerization inhibitors: These compounds can disrupt the normal functioning of tubulin, a protein essential for cell division, and are being explored for their potential in cancer therapy.
5. Peptide-mimetic protease-activated receptor-1 (PAR-1) antagonists: These molecules can block the activity of PAR-1, a receptor involved in various physiological processes, and may have applications in treating conditions like thrombosis and inflammation.
6. Cytosolic phospholipase A2α: This enzyme plays a role in the production of inflammatory mediators, and its inhibition can be beneficial in treating inflammatory diseases.
7. Cyclooxygenase (COX) inhibitors: These compounds can inhibit the activity of COX enzymes, which are involved in the production of prostaglandins, and are commonly used as anti-inflammatory and analgesic agents.
8. Serotonin 5-HT6 Receptor Ligands: These molecules can modulate the activity of the serotonin 5-HT6 receptor, which is implicated in various neurological and psychiatric disorders.
Used in Chemical Industry:
2-METHYL-5-NITROINDOLE is used as a building block for the synthesis of heterocyclic β-substituted alanine derivatives, which are important components in the development of novel pharmaceuticals and other chemical compounds with potential applications in various industries.

InChI:InChI=1/C9H8N2O2/c1-6-4-7-5-8(11(12)13)2-3-9(7)10-6/h2-5,10H,1H3

Upstream product

• 115210-54-3 2-methyl-5-nitroindoline 
• 95-20-5 2-methyl-1H-indole 
• 53512-36-0 2-Methyl-3-methylthio-5-nitroindol 
• 100-16-3 4-nitrophenylhydrazone 
• 67-64-1 acetone 
• 100-01-6 4-nitro-aniline 
• 1363421-86-6 2-methyl-5-azido-1H-indole 
• 75-05-8 acetonitrile 

Downstream Products

• 7570-49-2 5-amino-2-methylindole 
• 147646-73-9 3-benzyl-2-methyl-5-nitro-indole 
• 120627-43-2 2-methyl-5-nitro-1-(phenylmethyl)-1H-indole 
• 3558-17-6 2-Methyl-5-nitro-1H-indole-3-carboxaldehyde 
• 51226-47-2 1,2-dimethyl-5-nitro-1H-indole 
• 115210-54-3 2-methyl-5-nitroindoline 
• 852042-41-2 1-(3,5-dimethyl-phenyl)-2-methyl-5-nitro-1H-indole 
• 872675-11-1 1-(diphenylmethyl)-2-methyl-5-nitro-1H-indole 
• 872675-13-3 2-[1-(diphenylmethyl)-2-methyl-5-nitro-1H-indol-3-yl]ethanol 
• 872675-12-2 ethyl [1-(diphenylmethyl)-2-methyl-5-nitro-1H-indol-3-yl]oxoacetate 
• 872675-16-6 methyl 4-[2-[5-amino-1-(diphenylmethyl)-2-methyl-1H-indol-3-yl]ethoxy]benzoate 
• 872675-14-4 methyl 4-[2-[1-(diphenylmethyl)-2-methyl-5-nitro-1H-indol-3-yl]ethoxy]benzoate 
• 852042-43-4 1-(3,5-dimethyl-phenyl)-2-methyl-5-nitro-2,3-dihydro-1H-indole 
• 312305-94-5 benzyl (2R)-5-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-methyl-2,3-dihydro-1H-indole-1-carboxylate 

Relevant articles and documents

Trichloroisocyanuric acid (TCCA) and carboxamide interactions in TCCA/NaNO2 triggered nitration of pyrrole and indole in aqueous aprotic media: A kinetic correlation of solvent properties with reactivity

This study deals with the trichloroisocyanuric acid (TCCA) interactions with carboxamides like formamide (FMA), N,N′-dimethyl formamide (DMF), and N,N′-dimethyl acetamide (DMA) interactions during the nitration of heterocyclic compounds (HC) like pyrrole and indole in the presence of excess of [NaNO2] over the concentrations of all other reactants. All the reactions were performed in aqueous acetonitrile media containing carboxamide under acid-free conditions. Kinetics of the reactions revealed first order in [nitrating agent] and [HC] under otherwise similar conditions. To gain an insight into the reactive species and role of added carboxamide (FAA, DMF, DMA, etc.), the observed rates of the nitration reaction (log k) were analyzed as a function of (1/D), ([D ? 1]/[2D + 1]), mole fraction (nx), and volume (%) of carboxamide, 1/viscosity, density refractive index function), and Hildebrand solubility parameter plots. Linear regression analysis gave very good correlation coefficients (R2 values), which indicate the importance of several solvent properties in addition to the role of dielectric constant (D) of the reaction media. Multiple linear solvent energy relationships suggested by Abraham, Koppel, Palm, and Taft also afforded very good correlation coefficient (R2 values), showing the importance of cumulative effect of solvent properties. Besides these features, the negative entropies of activation (?S#) suggest greater solvation in the transition state. Isokinetic temperature (β) values for different protocols were very close to the experimental temperature range (303-323 K), indicating the importance of both enthalpy and entropy factors in controlling the reaction.

On the mechanism for the photooxidation of aromatic azides containing a secondary N–H bond: A sequence of intramolecular transformations with the formation of heterocyclic oximes

During the photooxidation of aromatic azides containing a secondary N–H bond at the para-position, a sequence of intramolecular transformations of nitroso oxides led to the formation of heterocyclic oximes along with the corresponding nitroso and nitro co

PROTEASOME ACTIVITY ENHANCING COMPOUNDS

The present invention is directed to compounds having the Formula (I), (II), (III), (IV), and (V), compositions thereof, the methods of synthesis of the compouds of interest, and to methods for the treatment of a condition associated with a dysfunction in proteostasis, such as cancer, inflammatory conditions, neurodegeneration, metabolic conditions, comprising administering an effective amount of a compound of the invention.