3882-46-0

Basic information

• Product Name: 4-AZA-9-FLUORENONE
• Synonyms: 5H-INDENO[1,2-B]PYRIDIN-5-ONE;4-AZA-9-FLUORENONE;AKOS 92850;Indeno[1,2-b]pyridin-5-one
• CAS NO: 3882-46-0
• Molecular Formula: C₁₂H₇NO
• Molecular Weight: 181.19
• EINECS: 223-414-5
• Mol File: 3882-46-0.mol

Chemical Properties

• Boiling Point: 361°Cat760mmHg
• Flash Point: 179.8°C
• Appearance: /
• Density: 1.312g/cm³
• Vapor Pressure: 2.14E-05mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: 4-AZA-9-FLUORENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AZA-9-FLUORENONE(3882-46-0)
• EPA Substance Registry System: 4-AZA-9-FLUORENONE(3882-46-0)

Safety Data

• Hazardous Substances Data: 3882-46-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-AZA-9-FLUORENONE is used as a versatile intermediate for the synthesis of various organic compounds due to its unique structural properties and reactivity.
Used in Pharmaceutical Industry:
4-AZA-9-FLUORENONE is used as a pharmaceutical intermediate for the development of new drugs, leveraging its unique chemical properties and potential biological activities.
Used in Materials Science:
4-AZA-9-FLUORENONE is used in the development of optical materials and sensors, capitalizing on its fluorescent and luminescent properties.
Used in Electronic Devices:
4-AZA-9-FLUORENONE is used in the fabrication of organic light-emitting diodes (OLEDs) and other electronic devices, owing to its potential applications in enhancing device performance and functionality.

InChI:InChI=1/C12H7NO/c14-12-9-5-2-1-4-8(9)11-10(12)6-3-7-13-11/h1-7H

Upstream product

• 244-99-5 4-azafluorene 
• 33421-39-5 2-phenyl-3-pyridinecarboxylic acid 
• 50555-86-7 4-aza-9-diazo-9H-fluorene 
• 120-92-3 cyclopentanone 
• 132464-43-8 N,N-Diisopropyl-2-pyridin-2-yl-benzamide 
• 65938-98-9 benzoquinoline-5,6-dione 
• 188797-88-8 methyl 2-phenylpyridine-3-carboxylate 
• 606-23-5 1H-indene-1,3(2H)-dione 
• 107-02-8 acrolein 
• 3882-45-9 2-nitrophenyl pyridin-3-yl ketone 
• 3882-48-2 2-aminophenyl-(3-pyridinyl)methanone 
• 3882-44-8 (2-nitrophenyl)(pyridin-3-yl)methanol 
• 552-89-6 2-nitro-benzaldehyde 
• 80099-85-0 2-chloro-3-(4-chlorobenzoyl)-pyridine 

Downstream Products

• 244-99-5 4-azafluorene 
• 80347-87-1 9-(p-Methoxyphenyl)-4-azafluoren-9-ol 
• 80347-88-2 9-(p-Ethoxyphenyl)-4-azafluoren-9-ol 
• 107046-91-3 9-benzyl-4-azafluoren-9-ol 
• 110576-19-7 4-Azafluorene-9-one semicarbazone 
• 89972-00-9 9-(β-phenylethylimino)-4-azafluorene 
• 87446-06-8 9-Phenylethynyl-4-azafluoren-9-ol 
• 120560-93-2 9-(1,2-dibenzoylethylidene)-4-azafluorene 
• 148711-80-2 9-(1',2'-dibenzoylethylidene)-4-azafluorene hydrochloride 
• 120533-54-2 9-phenacylidene-4-azafluorene 
• 65939-03-9 4-Azafluorenone oxime 
• 71483-73-3 4-aza-9-fluorenone tosylhydrazone 
• 80347-90-6 N-Methyl-9-(p-methoxyphenyl)-4-azafluorenium Iodide 
• 120533-56-4 9-hydroxy-9-(1'-hydroxy-1',2'-dibenzoylethyl-1')-4-azafluorene 

Relevant articles and documents

Synthesis of azafluorenone via oxidative intramolecular Heck cyclization

A very short and highly efficient protocol to azafluorenone exploiting intramolecular oxidative Heck cyclization using Pd(0) is presented. Precursor alcohols afforded azafluorenone in a single step with simultaneous oxidation and cyclization under Heck reaction condition in excellent yield. This methodology could be very much crucial in the total synthesis of azafluorenone alkaloids for promising pharmacological activity.

Synthesis of azafluorenones using zeolites

A convenient method for the synthesis of various azafluorenones (2a-f and 4a-d) by cyclization of substituted arylpyridines (1a-f and 3a-d) using zeolites are described.

Direct deoxygenative intramolecular acylation of biarylcarboxylic acids

A photocatalyzed intramolecular cyclization is developed for the synthesis of fluorenones. In this photoredox reaction, triphenylphosphine is used as an inexpensive and effective deoxygenative reagent for biarylcarboxylic acids to give acyl radicals, which quickly undergo intramolecular radical cyclization. Reactions in the presence of air and continuous flow photoredox technology demonstrate the generality and practicality of this process.

IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines

An iodoxybenzoic acid-mediated selected oxidative cyclization of N-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alcohol, followed by condensation of aldehyde and α-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally friendly reagents, broad substrate scope, mild reaction conditions, and high efficiency.

Organic electrophosphorescent material, preparation method, and OLED device containing the same (by machine translation)

Is an organic electro-phosphorescent material, a preparation method OLED thereof, and an organic electrophosphorescent material comprising the compound. of Formula I, or Formula II, wherein the compound of Formula III is a red light-emitting material. and the compound of Formula I is a red light-emitting material, of the present invention. II. The organic electrophosphorescent material of the present invention is easily sublimated and dissolved III for mass production . The present invention provides an organic electrophosphorescent material having a structure represented by the following formula: OLED. The organic electrophosphorescent material of the present invention is advantageous; in terms of efficiency. OLED. (by machine translation)

Compound and composition for forming organic film

The present invention provides a compound which is capable of curing to form an organic film even in an inert gas not only in air atmosphere without forming byproducts, and also forming an organic under layer film that has good dry etching durability in substrate processing, excels in heat resistance and possesses superior gap filling/planarizing characteristics of a pattern formed on a substrate.The compound is shown by the following general formula (1-1), wherein AR1 and AR2 each independently represent an aromatic ring or an aromatic ring that contains at least one nitrogen atom and/or sulfur atom, two AR1s, AR1 and AR2, or two AR2s are optionally bonded with each other; AR3 represents a benzene ring, a naphthalene ring, a thiophene ring, a pyridine ring, or a diazine ring; A represents an organic group; B represents an anionic leaving group; Y represents a divalent organic group; p is 1 or 2; q is 1 or 2; r is 0 or 1; s is 2 to 4; when s = 2, Z represents a single bond, a divalentatom, or a divalent organic group; and when s = 3 or 4, Z represents a trivalent or quadrivalent atom or organic group.

Azafluorenone derivative and preparation method and application thereof

The invention belongs to the technical field of organic synthesis and particularly relates to a polyfunctional-group-substituted azafluorenone derivative and a preparation method and application thereof. The structural formula of the azafluorenone derivative is shown as a formula (I), wherein Ar is an aryl group, the aryl group comprises an aromatic heterocyclic group, a phenyl group or aromatic fused ring group, R1 is selected from hydrogen, an ether group, halogen, acetyl, an ester group, trifluoromethyl or sulfuryl, and R2 is selected from hydrogen, alkyl, aryl, halogen, an ether group, trifluoromethyl, acetyl, an ester group or sulfuryl. By taking an aryl imido ester compound and olefin as substrates and under a metal catalysis effect, a cascade reaction of multiple times of aromatic ring carbon hydrogen bond activation based on aryl imine ester guidance and oxygen oxidation of alkyl carbon-carbon is achieved, and accordingly the poly-substituted azafluorenone derivative is rapidlyand modularly constructed. The azafluorenone medicine has a good application prospect in the development of organic photoelectric materials.

Sequential C-H and C-C Bond Cleavage: Divergent Constructions of Fused N-Heterocycles via Tunable Cascade

Streamlining the generation of diverse highly functionalized molecules from abundant feedstocks holds great synthetic promises and challenges in pharmaceutical and material discovery. Herein, we report a tunable selectivity in multiple cascade reactions for the divergent assembly of fused N-heterocycles, comprising sequential activation of C-H and C-C bonds. Isolatable indene-type intermediates might be responsible for the generation of densely substituted fused pyridines, azepines, and azafluorenones products. The tolerance of strongly coordinating N-heterocycles, and those readily applicable for the late-stage modifications of pharmaceuticals and material molecules precursors, further demonstrated the synthetic robustness of this transformation.

Nitrogen introduction of spirobifluorene to form α-, β-, γ-, and δ-aza-9,9′-spirobifluorenes: New bipolar system for efficient blue organic light-emitting diodes

Four aza-9,9′-spirobifluorenes (aza-SBFs) with nitrogen atom at different positions of one fluorene moiety were synthesized to study the structure-properties relationships. α-Aza-SBF and β-aza-SBF possessed almost completely separated the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), while γ-aza-SBF and δ-aza-SBF showed overlapped HOMO and LUMO orbitals. The aza-SBFs showed excellent bipolar features and good thermal stabilities than those of SBFs. The maximum current efficiencies (CE) of α-, β-, γ-, and δ-aza-SBF-based OLEDs were 28.8, 24.9, 25.5, and 27.2 cd/A, respectively. Compared to the SBF, all of four aza-SBFs showed better devices performances. The CE and power efficiency (PE) of OLED based on α-aza-SBF was 28.8 cd/A and 22.6 lm/W, while the SBF-based OLED was only 12.3 cd/A and 8.2 lm/W. The maximum external quantum efficiency of α-aza-SBF-based OLED was 15.4%, which was 2.5 times than that of the SBF-based one (6.6%) due to introduction of nitrogen improving electron transporting. Novel materials based on these components and their potential applications in organic electronics were expected due to their excellent bipolar features.

Scope of regioselective Suzuki reactions in the synthesis of arylpyridines and benzylpyridines and subsequent intramolecular cyclizations to azafluorenes and azafluorenones

The current investigation on regioselective Suzuki reactions of 2,3-dihalopyridines and 2-halo-3-halomethylpyridines yielded the unexplored synthesis of arylpyridines and benzylpyridines bearing synthetic handles for further functionalization. Indeed, the scope of intramolecular cyclizations of arylpyridines and benzylpyridines prepared in this study for the synthesis of azafluorenes and azafluorenones has been investigated.