6510-65-2

Basic information

• Product Name: 1-methyl-9H-carbazole
• Synonyms: 9H-carbazole, 1-methyl-; 9H-Carbazole, methyl-; Carbazole, 1-methyl-; METHYLCARBAZOLE
• CAS NO: 6510-65-2
• Molecular Formula: C₁₃H₁₁N
• Molecular Weight: 181.2331
• Mol File: 6510-65-2.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 369.1°C at 760 mmHg
• Flash Point: 165.4°C
• Density: 1.19g/cm³
• Vapor Pressure: 2.59E-05mmHg at 25°C
• Refractive Index: 1.736
• CAS DataBase Reference: 1-methyl-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-9H-carbazole(6510-65-2)
• EPA Substance Registry System: 1-methyl-9H-carbazole(6510-65-2)

Safety Data

• Hazardous Substances Data: 6510-65-2(Hazardous Substances Data)

Usage

General Description

1-methyl-9H-carbazole, also known as 1-methylcarbazole, is a chemical compound with the molecular formula C13H11N. It is a colorless to pale yellow solid that is insoluble in water but soluble in common organic solvents. 1-methyl-9H-carbazole is commonly used in the production of dyes, pigments, and pharmaceuticals. It has also been studied for its potential use in organic light-emitting diodes (OLEDs) and as an antioxidant in various materials. The compound is considered to have low toxicity and is not known to be a carcinogen or mutagen in humans. Overall, 1-methyl-9H-carbazole is a versatile and useful chemical with a range of industrial and research applications.

Upstream product

• 120-72-9 indole 
• 3209-78-7 5,5-dimethoxy-pentan-2-one 
• 17058-12-7 1-methyl-2,3,4,9-tetrahydro-1H-carbazole 
• 64-19-7 acetic acid 
• 1208-57-7 2-methylcyclohexanone phenylhydrazone 
• 854715-10-9 cyclohexanone-o-tolylhydrazone 
• 3449-50-1 8-methyl-2,3,4,9-tetrahydro-carbazol-1-one 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 91-22-5 quinoline 
• 19283-51-3 8-Methyl-1,2,3,4-tetrahydro-carbazol 
• 725234-49-1 1-o-toluidino-cyclopentanecarboxylic acid 
• 141-52-6 sodium ethanolate 
• 34897-85-3 o-azidobenzoyl chloride 

Downstream Products

• 86-74-8 9H-carbazole 
• 6311-19-9 9H-carbazole-1-carboxylic acid 
• 1903-94-2 9H-carbazole-1-carbaldehyde 
• 21240-57-3 3-formyl-1-methylcarbazole 

Relevant articles and documents

Secondary phosphine oxides assisted palladium complexes catalyzed catellani reaction for the formation of carbazole derivatives

Several secondary phosphine oxides (SPOs, 2a-2d) as well as 2a-chelated palladium complex 2a_Pd were employed in Catellani type reaction for the synthesis of 1-methyl-9H-carbazole (4) from 2-iodotoluene and N-(2-bromophenyl)acetamide (3). The application

A versatile carbazole donor design strategy for blue emission switching from normal fluorescence to thermally activated delayed fluorescence

The weak electron donating ability of carbazole is most suitable for constructing the donor-acceptor type blue emitters, but its low spatial requirements caused by the five-membered ring bridged structure is not favorable for spatial separation of frontier molecular orbitals. So many carbazole based compounds do not exhibit thermally activated delayed fluorescence (TADF). Herein, a more sterically demanding group was introduced at the 1-site of carbazole to form 1-methylcarbazole (1-MeCz), in order to construct a versatile donor for blue TADF materials. 1-MeCz was used as donor in combination with triazine and pyrimidine as acceptors to design novel compounds 1-MeCz-TRZ and 1-MeCz-Pm. It was observed that the presence of the methyl group at the 1-site of carbazole enhanced the twisted angles and reduced frontier molecular orbital overlapping, successfully switching the blue emission from the normal fluorescence of the methyl-free reference compounds (Cz-TRZ and Cz-Pm) to TADF of 1-MeCz-TRZ and 1-MeCz-Pm. The organic light-emitting diodes of 1-MeCz-TRZ and 1-MeCz-Pm exhibited blue emission at 450 and 458 nm with Commission Internationale de L'Eclairage (CIE) coordinates of (0.15, 0.11) and (0.17, 0.18), and external quantum efficiencies of 13.07% and 7.53%. This study provides a versatile, simple and practical design strategy with 1-MeCz to construct pure blue TADF emitters in combination with various acceptors.

Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids

An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.