111296-91-4

Basic information

• Product Name: 5H,12H-Indolo[3,2-a]carbazole
• Synonyms: 5,12-Dihydroindolo[3,2-a]carbazole;5H,12H-Indolo[3,2-a]carbazole;7,12-Dihydroindolo[3,2-c]carbazole;5,12-dihydroindolo[3,2-c]carbazole;Indolo[3,2-a]carbazole, 5,12-dihydro-;5,12-dihydroindolo[3,2-a]carbazole(98%+)
• CAS NO: 111296-91-4
• Molecular Formula: C₁₈H₁₂N₂
• Molecular Weight: 256.30128
• Mol File: 111296-91-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 299-300℃
• Boiling Point: 569.8±23.0 °C(Predicted)
• Appearance: /
• Density: 1.404±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 17.00±0.30(Predicted)
• CAS DataBase Reference: 5H,12H-Indolo[3,2-a]carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5H,12H-Indolo[3,2-a]carbazole(111296-91-4)
• EPA Substance Registry System: 5H,12H-Indolo[3,2-a]carbazole(111296-91-4)

Safety Data

• Hazardous Substances Data: 111296-91-4(Hazardous Substances Data)

Usage

General Description

5H,12H-Indolo[3,2-a]carbazole is a chemical compound that belongs to the class of polycyclic aromatic hydrocarbons. It is a heterocyclic compound containing carbon and nitrogen atoms in its ring structure. 5H,12H-Indolo[3,2-a]carbazole is known for its potential use in various applications such as organic semiconductor materials, organic light-emitting diodes, and as a potential anti-cancer agent. Its unique structure and properties make it a promising candidate for further research and development in the fields of material science and pharmaceuticals. Additionally, it is important to note that this compound may have potential health and environmental hazards, and appropriate safety precautions should be taken when handling and using it.

Upstream product

• 822-87-7 2-Chlorocyclohexanone 
• 120-72-9 indole 
• 6637-10-1 2,3-dihydro-1H,1'H-[2,3']biindolyl 
• 27393-85-7 3-(2-indolyl)indole 
• 69128-20-7 N-(2,2-diethoxyethyl)propan-2-ylamine 
• 504-02-9 1,3-cylohexanedione 
• 59-88-1 phenylhydrazine hydrochloride 
• 855738-89-5 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 9H-carbazole 
• 577-19-5 2-nitrophenyl bromide 
• 10268-78-7 1,3-diacetylaminobenzene 
• 108-45-2 m-phenylenediamine 
• 5905-36-2 N,N'-diphenyl-m-phenylenediamine 
• 3616-56-6 dimethylaminoacetaldehyde diethyl acetal 
• 143858-58-6 4-oxo-1,2,3,4-tetrahydrocarbazole phenylhydrazone hydrochloride 

Downstream Products

• 1247053-55-9 5,12-dihydro-5-phenyl indolo[3,2-a]carbazole 
• 1247053-56-0 C₃₅H₂₃N₃ 
• 1448304-58-2 C₄₈H₃₁N₃ 

Relevant articles and documents

Reactions of 2,3'-biindolyl: Synthesis of indolo[3,2-a]carbazoles

2,3'-Biindolyl (9) has been transformed into indolo[3,2-a]carbazoles 16a-b by means of formal [4 + 2] cycloadditions with co-formation of the Michael adducts 17a-b. The parent indolo[3,2-a]carbazole (6) has been prepared in one step from 9 in excellent yield. Several 3-substituted 2,3'- biindolyls have also been prepared in good yields and underwent further transformations, demonstrating the versatility of 2,3'-biindolyl (9) as a building block for synthesis of indolo[3,2-a]carbazoles.

Synthesis of 2-(9H-carbazol-1-yl)anilines from 2,3′-biindolyl and ketones

Twenty-nine examples of 2-(9H-carbazol-1-yl)anilines were obtained in yields from 27 to 95% by refluxing 2,3′-biindolyl (1 equiv.) and ketones (1 equiv.) in ethanolic HCl. Alkyl, cyclic, and aryl ketones were found to be compatible with this method, however, aldehydes are not. Because the reaction proceeds by addition of the carbonyl C atom to the biindolyl 3-position, this method has high regioselectivity. One example is presented of bridging the two N atoms in the carbazolylaniline product with an acetaldehyde synthon to give a benzodiazepino[lm]carbazole. Also, one example is given of installing a dimethylamino group at the α-position of the starting ketone to give an indolo[3,2-c]carbazole.

Synthetic method of indolocarbazole derivative and preparation method of long afterglow material of indolocarbazole derivative

The invention discloses a synthetic method of an indolocarbazole derivative. The synthetic method is characterized in that a reaction formula is shown in a formula 1 or other formulas 4. The novel method is used for synthesizing the indolocarbazole derivative, so that the reaction time is greatly shortened, the yield is improved, and the production cost is reduced.

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).