61166-05-0

Basic information

• Product Name: 9-METHYL-3-NITRO-9H-CARBAZOLE
• Synonyms: 9-methyl-3-nitro-9h-carbazol;9-METHYL-3-NITRO-9H-CARBAZOLE;3-NITRO-9-METHYLCARBAZOLE
• CAS NO: 61166-05-0
• Molecular Formula: C₁₃H₁₀N₂O₂
• Molecular Weight: 226.23
• Mol File: 61166-05-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 172 °C
• Boiling Point: 349.1°C at 760 mmHg
• Flash Point: 164.9°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 4.8E-05mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: 9-METHYL-3-NITRO-9H-CARBAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-METHYL-3-NITRO-9H-CARBAZOLE(61166-05-0)
• EPA Substance Registry System: 9-METHYL-3-NITRO-9H-CARBAZOLE(61166-05-0)

Safety Data

• Hazardous Substances Data: 61166-05-0(Hazardous Substances Data)

Usage

General Description

9-Methyl-3-nitro-9H-carbazole is a chemical compound with the formula C15H11N3O2. It is a nitro-substituted derivative of carbazole, a heterocyclic aromatic compound. 9-METHYL-3-NITRO-9H-CARBAZOLE finds applications in various fields, including organic synthesis and materials science. It is used as a building block in the preparation of organic compounds and as a starting material for the synthesis of various derivatives. Additionally, it has been studied for its potential use in organic electronic devices and materials due to its unique electronic and optical properties. Its structure and properties make it of interest for further research and development in the fields of chemistry and materials science.

InChI:InChI=1/C13H10N2O2/c1-14-12-5-3-2-4-10(12)11-8-9(15(16)17)6-7-13(11)14/h2-8H,1H3

Upstream product

• 1484-12-4 N-methylcarbazole 

Downstream Products

• 61166-04-9 3-amino-N-methylcarbazole 
• 180331-84-4 N-(9-methyl-carbazol-3-yl)-acetamide 
• 94127-15-8 3-(N,N-dimethylamino)-9-methylcarbazole 
• 5416-98-8 3-(N-methylamino)-9-methylcarbazole 

Relevant articles and documents

Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C-Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C-H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under mild conditions occurred predominantly at the electron-rich position. The resulting product having methoxy and bromo groups can be utilized as a building block for the synthesis of unsymmetrically substituted 9-silafluorene-containing π-conjugated molecules.

Halogenating and nitrating activity of reagents based on sodium nitrate and alkali metal halides in acetic acid

Alkali metal halides NaF, KCl, and KBr sharply enhance the nitrating activity of sodium nitrate in acetic acid with respect to 9-methylcarbazole. In the presence of KI and KBr, both nitration and halogenation of the substrate occurs, while KCl and NaF promote only the nitration process. The results may be interpreted in terms of formation of the corresponding nitryl halides XNO2 (X = F, Cl, Br, I) whose structure and reactivity were examined in the framework of the density functional theory (DFT B3LYP/3-21G*).

Nitration of the Acetanilide-type Compounds

Some aromatic compounds containing the imino group (NH) were nitrated in acetic acid or anhydride, and the ortho/para ratios were measured.N-Methyl derivatives of the aforementioned compounds are much less reactive when nitrated under comparable conditions and give significantly lower o/p ratios.These results along with the literature data support the hypothesis that the acetanilide-type compounds are nitrated via N-nitro intermediates.