3652-91-3

Basic information

• Product Name: 2-METHYLCARBAZOLE
• Synonyms: 2-METHYLCARBAZOLE;2-Methyl-9H-carbazole;2-Methyldibenzopyrrole;Carbazole, 2-methyl-
• CAS NO: 3652-91-3
• Molecular Formula: C₁₃H₁₁N
• Molecular Weight: 181.23
• EINECS: 222-894-3
• Mol File: 3652-91-3.mol
• Article Data: 54

Chemical Properties

• Melting Point: 259 °C
• Boiling Point: 369.1°Cat760mmHg
• Flash Point: 165.4°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 2.59E-05mmHg at 25°C
• Refractive Index: 1.736
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 17.15±0.30(Predicted)
• CAS DataBase Reference: 2-METHYLCARBAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLCARBAZOLE(3652-91-3)
• EPA Substance Registry System: 2-METHYLCARBAZOLE(3652-91-3)

Safety Data

• Hazardous Substances Data: 3652-91-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 44, p. 5215, 1988 DOI: 10.1016/S0040-4020(01)86029-4

InChI:InChI=1/C13H11N/c1-9-6-7-11-10-4-2-3-5-12(10)14-13(11)8-9/h2-8,14H,1H3

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 78-94-4 methyl vinyl ketone 
• 123-31-9 hydroquinone 
• 21240-53-9 7-methyl-2,3,4,9-tetrahydro-1H-carbazole 
• 6286-54-0 2-methyl-1,2,3,4-tetrahydro-9H-carbazole 
• 1205-64-7 3-Methyldiphenylamine 
• 3417-69-4 2-(2-methylprop-1-enyl)-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 13194-69-9 2-iodo-5-methylaniline 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 14385-93-4 2-iodo-4'-methylbiphenyl 
• 14680-38-7 2-iodo-4-methyl-1,1'-biphenyl 
• 16863-96-0 3-chloro-1H-indole 
• 14192-61-1 2-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 

Downstream Products

• 126479-96-7 9-benzenesulfonyl-2-(1-naphthylethyl)carbazole 
• 126479-97-8 9-benzenesulfonyl-2-(2-naphthylethyl)carbazole 
• 126479-90-1 9-benzenesulfonyl-2-(1-naphthylethenyl)carbazole 
• 126479-91-2 9-benzenesulfonyl-2-(2-naphthylethenyl)carbazole 
• 126479-86-5 2-dibromomethyl-9-benzenesulfonylcarbazole 
• 126479-88-7 9-benzenesulfonyl-2-carbazolecarboxaldehyde 
• 152499-81-5 2-Acetylamino-2-(9-benzoyl-9H-carbazol-2-ylmethyl)-malonic acid diethyl ester 
• 152499-79-1 9-benzoyl-2-bromomethylcarbazole 
• 116325-34-9 2-methyl-9-benzenesulfonylcarbazole 
• 152499-78-0 9-benzoyl-2-methylcarbazole 

Relevant articles and documents

Benzoannelation of 2-methylindole via 1-N-carboxy-2-methylindole dianion: A direct regiospecific route to substituted and annelated carbazoles

A facile general route for substituted and annelated N-H- carbazoles 6 has been developed by regiospecific 1,2-addition of 1- N-carboxy-2-methylindole dianion 3 to acyclic and cyclic α-oxoketene dithioacetals 4 followed by cycloaromatization in the presence of H3PO4.

Convenient One-Pot Synthesis of 9 H -Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst

An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald-Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9 H -carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.

Total synthesis of carbazole alkaloids

A Suzuki-Miyaura cross coupling, followed by triphenylphosphine mediated Cadogan reductive cyclization sequence provided efficient access to a series of carbazole alkaloids. In the present work, this approach was applied to the total synthesis of mukonine, clauszoline K, koenoline, murrayanine, murrayafoline A, mukoeic acid, glycoborine, glycozolicine, mukolidine, mukoline, glycozoline, 3-methoxy-9H-carbazole-1-carboxylic acid methyl ester, (3-methoxy-9H-carbazol-1-yl)-methanol, 3-methoxy-9H-carbazole-1-carbaldehyde, 3-methoxy-9H-carbazole-1-carboxylic acid, 2-methyl-9H-carbazole and nonsteroidal anti-inflammatory drug (NSAID) carprofen and its derivatives.

Preparation of 2 - substituted oxazole compounds

The present invention belongs to the field of organic chemistry, and particularly relates to a preparation method for 2-substituted carbazole compounds. According to the preparation method provided by the present invention, the raw material source is wide, reaction operation and post-treatment are simple and convenient, the yield is high, the application range is wide, and the industrial production is facilitated.