2041-27-2

Usage

Uses

Used in Organic Synthesis:
2,3-Dimethoxy-9H-fluoren-9-one is used as a building block in organic synthesis for its versatile chemical properties and potential to form various derivatives.
Used in Optoelectronic Devices:
In the Optoelectronics Industry, 2,3-Dimethoxy-9H-fluoren-9-one is used as a component in the development of organic light-emitting diodes (OLEDs) and other devices, leveraging its high thermal stability and efficient electron transport capabilities.
Used in Pharmaceutical Research:
2,3-Dimethoxy-9H-fluoren-9-one is used as a subject of interest in pharmaceutical research for its potential anti-inflammatory and antioxidant properties, which could contribute to the development of new therapeutic agents.
Despite its potential applications, 2,3-Dimethoxy-9H-fluoren-9-one is not widely used in commercial products and remains primarily a compound of interest for research purposes.

Upstream product

• 91-16-7 1,2-dimethoxybenzene 
• 6311-23-5 2-(toluene-4-sulfonylamino)-benzoic acid 
• 59142-61-9 2-benzoyl-4, 5-dimethoxyl-1-bromobenzene 
• 26260-02-6 2-iodobenzaldehyde 
• 866252-52-0 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 61203-53-0 2-iodo-4,5-dimethoxybenzaldehyde 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 201230-82-2 carbon monoxide 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 583-55-1 1-Bromo-2-iodobenzene 
• 1794-58-7 3',4'-dimethoxy-[1,1'-biphenyl]-2-carboxylic acid 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 2042-37-7 o-cyanobromobenzene 
• 124-38-9 carbon dioxide 

Relevant academic research and scientific papers

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.

Spirocentric Compounds and Polymers Thereof

The present invention is directed to novel functionalized spirocentric compounds and polymers thereof that produce hyper-rigid cross-linked membranes.

Palladium-catalyzed synthesis of fluoreones from bis(2-bromophenyl)methanols

A palladium-catalyzed synthesis method of fluorenones has been developed. A variety of bis(2-bromophenyl)methanols could undergo the reaction smoothly in the presence of Pd(OAc)2, affording a series of fluorenones in moderate to good yields (two steps). Mechanistic studies reveal that the reaction might be triggered by oxidation of alcohol followed by intramolecular reductive coupling.

The synthesis, chain-packing simulation and long-term gas permeability of highly selective spirobifluorene-based polymers of intrinsic microporosity

Membranes composed of Polymers of Intrinsic Microporosity (SBF-PIMs) have potential for commercial gas separation. Here we report a combined simulation and experimental study to investigate the effect on polymer microporosity and gas permeability by placing simple substituents such as methyl, t-butyl and fused benzo groups onto PIMs derived from spirobifluorene (PIM-SBFs). It is shown that methyl or t-butyl substituents both cause a large increase in gas permeabilities with four methyl groups enhancing the concentration of ultramicropores (a greater concentration of larger, less selective, micropores (>1.0 nm). Long-term ageing studies (>3.5 years) demonstrate the potential of PIM-SBFs as high-performance membrane materials for gas separations. In particular, the data for the PIM derived from tetramethyl substituted SBF reaches the proposed 2015 Robeson upper bound for O2/N2 and, hence, hold promise for the oxygen or nitrogen enrichment of air. Mixed gas permeation measurements for CO2/CH4 of the aged PIM-SBFs also demonstrate their potential for natural gas or biogas upgrading.

Palladium-catalyzed cyclocarbonylation of cyclic diaryliodoniums: Synthesis of fluorenones

An efficient approach to the synthesis of fluorenones via the palladium-catalyzed cyclocarbonylation of cyclic diaryliodoniums was developed. Our route enables facile access to fluorenones with various substituents in modest to high yields.

Metal free TBHP-promoted intramolecular carbonylation of arenes: Via radical cross-dehydrogenative coupling: Synthesis of indenoquinolinones, 4-azafluorenones and fluorenones

A metal-free, TBHP-promoted economical route is developed via the sp2 C-H bond functionalization strategy for the synthesis of indenoquinolinones, 4-azafluorenones and fluorenones. Reactions provided excellent yield of the products under mild conditions. We have successfully synthesized 11H-indeno[1,2-b]quinolin-11-one, an antibacterial agent, in excellent yields.

Domino Oxidative [Pd]-Catalysis: One-Pot Synthesis of Fluorenones Starting from Simple Benzylamines and Iodo Arenes

A domino [Pd]-catalysis for the efficient synthesis of fluorenones is presented. The overall reaction proceeds through the formation of a five membered Pd(II)-cycle via a highly regioselective ortho C(sp2)-H activation(s) of simple benzylamine that combines with external iodo arenes to give ortho arylated products. Significantly, the reaction further activates the C(sp3)-H and C(sp2)-H (intramolecular oxidative Heck coupling) bonds to give tricyclic imine systems. Then the usual water workup affords the fused tricyclic ketones (fluorenones). Remarkably, this one-pot operation enabled the effective construction of two C-C to three C-C bonds

Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol

Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel-Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential reaction mechanisms are reported.

Cross dehydrogenative coupling via base-promoted homolytic aromatic substitution (BHAS): Synthesis of fluorenones and xanthones

Cross dehydrogenative coupling reactions occurring via base-promoted homolytic aromatic substitutions (BHASs) are reported. Fluorenones and xanthones are readily prepared via CDC starting with readily available ortho-formyl biphenyls and ortho-formyl biphenylethers, respectively. The commercially available and cheap tBuOOH is used as an oxidant. Initiation of the radical chain reaction is best achieved with small amounts of FeCp2 (0.1 or 1 mol %).

Regioselective ortho-arylation and alkenylation of N-alkyl benzamides with boronic acids via ruthenium-catalyzed C-H bond activation: An easy route to fluorenones synthesis

A highly regioselective ruthenium-catalyzed ortho-arylation of substituted N-alkyl benzamides with aromatic boronic acids in the presence of [{RuCl 2(p-cymene)}2], AgSbF6, and Ag2O is described. Further, ortho-arylated N-alkyl benzamides were converted into fluorenones in the presence of trifluoroacetic anhydride and HCl.