243-38-9

Basic information

• Product Name: 11H-10,11-DIAZA-BENZO[B]FLUORENE
• Synonyms: 11H-10,11-DIAZA-BENZO[B]FLUORENE;5H-quinindoline;6H-indolo[2,3-b]quinoline
• CAS NO: 243-38-9
• Molecular Formula: C₁₅H₁₀N₂
• Molecular Weight: 218.2533
• EINECS: 205-954-3
• Mol File: 243-38-9.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 468.2 °C at 760 mmHg
• Flash Point: 217.5 °C
• Appearance: /
• Density: 1.336 g/cm³
• Vapor Pressure: 1.71E-08mmHg at 25°C
• Refractive Index: 1.839
• CAS DataBase Reference: 11H-10,11-DIAZA-BENZO[B]FLUORENE(CAS DataBase Reference)
• NIST Chemistry Reference: 11H-10,11-DIAZA-BENZO[B]FLUORENE(243-38-9)
• EPA Substance Registry System: 11H-10,11-DIAZA-BENZO[B]FLUORENE(243-38-9)

Safety Data

• Hazardous Substances Data: 243-38-9(Hazardous Substances Data)

Usage

General Description

11H-10,11-DIAZA-BENZO[B]FLUORENE, also known as dibenzofuranimine, is a chemical compound with a molecular formula C13H9N. It is a fused heterocyclic compound, containing two nitrogen atoms and a benzene ring in a linear configuration. This chemical is commonly used as a building block in the synthesis of various organic compounds, especially in the pharmaceutical industry. It has also been studied for its potential use in materials science, particularly in the development of organic semiconductor materials. Additionally, 11H-10,11-DIAZA-BENZO[B]FLUORENE has been investigated for its potential biological activities, including antibacterial and antiviral properties. Overall, this compound has shown potential in various industries and continues to be a subject of research and development.

InChI:InChI=1/C15H10N2/c1-3-7-13-10(5-1)9-12-11-6-2-4-8-14(11)17-15(12)16-13/h1-9H,(H,16,17)

Upstream product

• 942-24-5 3-methoxycarbonylindole 
• 612-62-4 2-Chloroquinoline 
• 22751-23-1 (2-nitrophenyl)acetyl chloride 
• 223906-76-1 3-[(2-nitrophenyl)methylidene]-1,3-dihydro-2H-indol-2-one 
• 91-56-5 indole-2,3-dione 
• 23308-83-0 (2-nitrobenzyl)triphenylphosphonium bromide 
• 5784-95-2 2-(4-methoxyphenyl)-1H-indole 
• 5670-66-6 1-nitro-2-(2-nitrovinyl)benzene 
• 95-20-5 2-methyl-1H-indole 
• 476-34-6 isoindigo 
• 223379-82-6 6-tosyl-6H-indolo[2,3-b]quinoline 
• 128676-97-1 3-(2-aminophenyl)-2-chloroquinoline 
• 112181-38-1 2,3-Bis(2-nitrophenyl)propanenitrile 
• 860719-30-8 2,4-dichloro-3-(2-nitro-phenyl)-quinoline 

Downstream Products

• 114414-78-7 neocryptolepine 

Relevant articles and documents

An improved synthesis of neocryptolepine

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Microwave-induced bismuth(III)-catalyzed synthesis of linear indoloquinolines

Microwave-induced Bi(NO3)3-catalyzed one-pot synthesis of a series of linear indoloquinolines is accomplished under mild reaction conditions. While majority of these examples were carried out under solvent-free conditions, in a few cases, minimal quantity of THF is used as solvent. The methodology involves several unique reaction pathways, providing different linear indolo[2,3-b]quinolines in good yields from readily available starting materials and using environmentally benign Bi(NO3)3·5H2O as catalyst.

N-Bromosuccinimide as an efficient catalyst for the synthesis of indolo[2,3-b]quinolines

The use of N-bromosuccinimide as a catalyst promoted the synthesis of polycyclic indolo[2,3-b]quinoline derivatives in good to high yields in the reactions of various aryl amines with indole-3-carbaldehyde at room temperature under mild conditions.

Tandem Rh(III)-Catalyzed C-H Amination/Annulation Reactions: Synthesis of Indoloquinoline Derivatives in Water

An efficient Rh(III)-catalyzed synthetic method for indoloquinoline derivatives from readily available indoles and isoxazoles was developed. This annulation procedure undergoes tandem C-H activation, cyclization, and condensation steps. In this domino cyclization reaction, water is an efficient solvent. A catalytically competent five-membered rhodacycle has been isolated and characterized, thus revealing a key intermediate in the catalytic cycle.

Synthetic studies towards benzofuro[2,3-b]quinoline and 6H-indolo[2,3-b]quinoline cores: Total synthesis of norneocryptolepine and neocryptolepine

An innovative acid-assisted cascade transformation of indoles with 2-nitrostyrenes was developed, allowing for the one-pot assembly of heterocyclic scaffolds with four fused rings. This strategy was subsequently employed for the concise total synthesis of two natural products, the alkaloids norneocryptolepine and neocryptolepine.

Acid mediated coupling of aliphatic amines and nitrosoarenes to indoles

Traditionally, amines react with nitrosoarenes to provide the corresponding imines or azo compounds. Herein, we report an acid mediated annulation reaction of aliphatic amines and nitrosoarenes to provide indole derivatives. The elusive direct annulation of aliphatic amines and nitrosoarenes via simultaneous C-C and C-N bond formation was achieved under metal free conditions. This conceptually novel method for indole synthesis does not require pre-functionalization steps for the new C-C and C-N bond formation. The method has been applied for an elegant synthesis of nor-neocryptolepine and neocryptolepine.

Synthesis of Indolo-and Benzothieno[2,3-b]quinolines by a Cascade Cyclization of o-Alkynylisocyanobenzene Derivatives

A new synthetic approach for the synthesis of indolo[2,3-b]quinolines and benzothieno[2,3-b]quinolines has been developed by employing the freshly prepared o-alkynylisocyanobenzenes derived from o-alkynylformamide derivatives as substrates. The synthetic transformations involved chloride-ion-triggered 6-endo cyclization of o-alkynylisocyanobenzenes to generate 2-chloroquinolines in situ, which further cyclized intramolecularly with nitrogen or sulfur atom via a cascade process to provide the corresponding indolo[2,3-b]quinolines and benzothieno[2,3-b]quinolines, respectively, in moderate to excellent yields.