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 
• 4652-27-1 4-methoxy-3-buten-2-one 
• 1205-64-7 3-Methyldiphenylamine 
• 3417-69-4 2-(2-methylprop-1-enyl)-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 108-44-1 1-amino-3-methylbenzene 
• 822-87-7 2-Chlorocyclohexanone 
• 73910-75-5 7-methyl-1-oxo-1,2,3,4-tetrahydrocarbazole 
• 91901-92-7 4-Methyl-2-azidobiphenyl 
• 262606-97-3 2-(phenyl-m-tolyl-amino)-isoindole-1,3-dione 

Downstream Products

• 152499-78-0 9-benzoyl-2-methylcarbazole 
• 116325-34-9 2-methyl-9-benzenesulfonylcarbazole 
• 152499-79-1 9-benzoyl-2-bromomethylcarbazole 
• 152499-81-5 2-Acetylamino-2-(9-benzoyl-9H-carbazol-2-ylmethyl)-malonic acid diethyl ester 
• 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 

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.

Visible-light-driven Cadogan reaction

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

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.