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

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

Uses

Used in Organic Synthesis:
9-METHYL-3-NITRO-9H-CARBAZOLE is used as a building block for the preparation of various organic compounds. Its versatile structure allows for the synthesis of a wide range of derivatives, contributing to the development of new chemical entities with potential applications in various industries.
Used in Materials Science:
In the field of materials science, 9-METHYL-3-NITRO-9H-CARBAZOLE serves as a starting material for the synthesis of advanced materials with unique properties. Its incorporation into materials can lead to the development of new products with improved performance characteristics.
Used in Organic Electronic Devices:
9-METHYL-3-NITRO-9H-CARBAZOLE has been studied for its potential use in organic electronic devices due to its electronic and optical properties. Its integration into these devices can enhance their performance and contribute to the advancement of organic electronics.
Used in Research and Development:
The structure and properties of 9-METHYL-3-NITRO-9H-CARBAZOLE make it an interesting subject for further research and development in the fields of chemistry and materials science. Its exploration can lead to the discovery of new applications and the creation of innovative products.

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

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.

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 ?-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*).

A new method of nitration of carbazoles using ceric ammonium nitrate (CAN)

A convenient procedure for the mononitration of carbazole and 9-alkylcarbazoles using CAN in CH3CN in presence of SiO2 is reported. The results with 9-acetyl, 9-benzoyl and 9- benzenesulphonylcarbazoles are also discussed.

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.