56525-80-5

Basic information

• Product Name: 5,11-dimethyl-5,11-dihydroindolo[3,2-b]carbazole
• Synonyms: 5,11-Dimethyl-5,11-dihydroindolo[3,2-b]carbazole; indolo[3,2-b]carbazole, 5,11-dihydro-5,11-dimethyl-
• CAS NO: 56525-80-5
• Molecular Formula: C₂₀H₁₆N₂
• Molecular Weight: 284.3544
• Mol File: 56525-80-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 526.6°C at 760 mmHg
• Flash Point: 272.3°C
• Density: 1.22g/cm³
• Vapor Pressure: 3.51E-11mmHg at 25°C
• Refractive Index: 1.699
• CAS DataBase Reference: 5,11-dimethyl-5,11-dihydroindolo[3,2-b]carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5,11-dimethyl-5,11-dihydroindolo[3,2-b]carbazole(56525-80-5)
• EPA Substance Registry System: 5,11-dimethyl-5,11-dihydroindolo[3,2-b]carbazole(56525-80-5)

Safety Data

• Hazardous Substances Data: 56525-80-5(Hazardous Substances Data)

Upstream product

• 6336-32-9 5H,11H-indolo[3,2-b]carbazole 
• 74-88-4 methyl iodide 
• 180331-85-5 (9-Methyl-9H-carbazol-3-yl)-phenyl-amine 
• 17754-68-6 N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine 
• 180331-84-4 N-(9-methyl-carbazol-3-yl)-acetamide 
• 61166-04-9 3-amino-N-methylcarbazole 
• 19012-03-4 N-methyl-3-formylindole 
• 86885-08-7 9-methyl-3-(N-methylanilino)carbazole 

Relevant articles and documents

A General and Facile Synthesis of Heterocyclo-Fused Carbazoles

1-Methyl-2-bromo-3-indole (2), available from the regioselective bromination of 1-methyl-3-indole (1), undergoes halogen-lithium exchange with t-BuLi.The resulting carbanion 4 reacts with thiophene-3-carboxaldehyde, furan-3-carboxaldehyde, thiophene-2-carboxaldehyde, furan-2-carboxaldehyde, and indole-3-carboxaldehyde.Subsequent quenching with methyl iodide affords the corresponding methyl ether intermediates 6a-e in excellent yields.Refluxing intermediates 6a-e in 1,2,4-trichlorobenzene or 1,2-dichlorobenzene causes intramolecular cyclization followed by aromatization. 5-Methylthienocarbazole (8a), 5-methylfurocarbazole (8b), 5-methylthienocarbazole (8c), 5-methylfurocarbazole (8d), and 5,11-dimethylindolocarbazole (8e) are thus obtained in 31-67percent yields.

From ascorbigens to indolocarbazoles

New methods of L-ascorbic acid derivatization with the use of polyfunctional indole-3-cabinols are described. Reaction of β-hydroxy-N-methyltryptamine and L-ascorbic acid gave lactame derivatives; (indol-3-yl)gylcolic and L-ascorbic acids produced 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)-)-cylopen-2-enone. Similarly 4-hydroxy-3-methoxyphenylglycolic and L-ascorbic acids yielded 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-4-hydroxymethyl-cyclopen-2-enone. Properties of N-methoxyascorbigen (neoascorbigen) were investigated. Alkylation of L-ascorbic acid with polysubstituted pyrrolecarbinols led to pyrrole analogues of ascorbigen. Acidic transformation of 3-formylindole and 1-methyl-3-formylindole led to indolocarbazoles and triindolylmethane derivatives.

An expedient synthesis of 5,11-dimethylindolo[3,2-b]-carbazole, a potent ligand for the receptor for TCDD

A new and efficient synthesis has been developed for the title indolocarbazole which has been indicated by a recent computer-aided study to be a potent ligand for the receptor for the naturally occurring carcinogen, TCDD.