7495-98-9

Usage

Uses

Used in Research and Development:
4-CNPM is used as a building block in the synthesis of various organic compounds and pharmaceuticals, contributing to the development of new drugs and chemical products. Its unique structure allows for the creation of a wide range of molecules with potential applications in different fields.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-CNPM is used as a precursor for the exploration of its structure-activity relationship and potential bioactivity. This research aims to understand how the compound interacts with biological targets and how it can be modified to enhance its therapeutic effects.
Used in the Production of Designer Drugs:
Although it is a regulated substance, 4-CNPM is known for its potential use as a precursor in the production of designer drugs. This application, however, is subject to strict control and regulation due to the potential risks associated with the misuse of such substances.

Upstream product

• 613-46-7 2-naphthalenecarbonitrile 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 32316-92-0 naphthalene-2-boronic acid 
• 122-01-0 4-chloro-benzoyl chloride 
• 790-41-0 4-chlorobenzoic anhydride 
• 91-20-3 naphthalene 
• 580-13-2 2-bromonaphthalene 
• 104-88-1 4-chlorobenzaldehyde 
• 1679-18-1 4-Chlorophenylboronic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 623-03-0 4-Cyanochlorobenzene 
• 2243-57-4 2-hydrazinonaphthalene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 147022-24-0 (4-chlorophenyl)(naphthalene-2-yl)methanol 
• 3042-67-9 2-(4-chlorobenzyl)naphthalene 
• 147022-12-6 1-[(4-Chloro-phenyl)-naphthalen-2-yl-methyl]-1H-imidazole 
• 70557-76-5 2-(4-chlorobenzyl)-1,4-naphthoquinone 

Relevant academic research and scientific papers

Beyond the Corey–Chaykovsky Reaction: Synthesis of Unusual Cyclopropanoids via Desymmetrization and Thereof

Desymmetrization-based protocols for the synthesis of highly functionalized indeno-spirocyclopropanes and cyclopropa-fused indanes have been established through unexpected reactions triggered by the Corey–Chaykovsky reagent. These structures were further elaborated in one step to privileged scaffolds such as fluorenones, indenones, and naphthaphenones. For instance, an acid-catalyzed transformation of indeno-spirocyclopropanes provided fluorenones via a homo-Nazarov-type cyclization, and naphthaphenones were obtained via an acid-catalyzed cyclopropane ring-opening/retro-Michael sequence.

Transition-Metal-Free Carbonylative Suzuki-Miyaura Reactions of Aryl Iodides with Arylboronic Acids Using N-Formylsaccharin as CO Surrogate

Unprecedented, high yielding, transition-metal-free carbonylative Suzuki-Miyaura reactions of aryl iodides with arylboronic acids using N-formylsaccharin as CO surrogate have been developed. Notably, this general protocol was adapted to the synthesis of the triglyceride and cholesterol regulator drug, fenofibrate, and carbon-13 labeled biaryl ketone. (Figure presented.).

Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of Arylboronic Acids and α-Iminonitriles through C–CN Bond Activation

A Pd-catalyzed Suzuki–Miyaura cross-coupling reaction between arylboronic acids and α-iminonitriles has been developed. The reaction proceeds through selective activation of the C–CN bond, tolerates a wide range of substituents, and delivers the versatile ketone products in moderate to excellent yields.

Palladium-Catalyzed Denitrogenative Synthesis of Aryl Ketones from Arylhydrazines and Nitriles Using O2 as Sole Oxidant

An efficient and simple palladium-catalyzed approach for the synthesis of aryl ketones from low-cost nitriles and arylhydrazines using molecular oxygen (O2) as sole oxidant via C-N bond cleavage is reported. Various aryl ketones were synthesized in moderate to good yields under mild conditions. A possible mechanism involving the PdII/Pd0 catalytic cycle process is depicted, and a cationic palladium intermediate was detected by ESI-MS.

Transition-metal-free, ambient-pressure carbonylative cross-coupling reactions of aryl halides with potassium aryltrifluoroborates

We disclose an unprecedented transition-metal-free carbonylative cross coupling of aryl halides with potassium aryl trifluoroborates even at atmospheric pressure of carbon monoxide. This protocol is efficient, operationally simple, and shows wide scope with regard to both aryl halides and potassium aryl trifluoroborates containing a series of active functional groups.

Facile preparation of aromatic ketones from aromatic bromides and arenes with aldehydes

Aromatic ketones were efficiently prepared in good yields by the reactions of aryl bromides with n-BuLi, followed by the reactions with aromatic aldehydes or aliphatic aldehydes and the subsequent treatment with molecular iodine and K2CO3, in a one-pot method. The same treatment of arenes, instead of aromatic bromides, also provided the corresponding aromatic ketones in good yields. Using these methods, various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatics and electron-deficient aromatics could be prepared efficiently by a simple, transition-metal-free, and therefore environmentally benign experimental procedure.

Solvent-free C-benzoylation and N-benzoylation reactions using

An ecofriendly and efficient microwave-irradiated solvent-free benzoylation method was developed. The procedure for C-benzoylation used 50 mol% AlCl 3 as a Lewis acid catalyst at 130°C and was completed in 10 min. The isolated yield was between 71% and 100%. N-benzoylation was conducted in a catalyst-free environment at 130°C in 10 min. The isolated yield was between 80% and 100%. Taylor & Francis Group, LLC.

The surfactant-promoted cross-coupling reactions of arylboronic acids with carboxylic anhydrides or acyl chlorides in water

The palladium(II) chloride catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides in water in the presence of various surfactants is described. The inexpensive and industrially widely used sodium dodecyl sulfate (SDS) was found to be a good promoter of the coupling reaction and aryl ketones were obtained in good yields without the use of phosphine ligands. The reactions were unaffected by the presence of electron-releasing and electron-withdrawing substituents in both the arylboronic acids and carboxylic derivatives and a variety of aryl ketones were obtained under mild conditions in air. Georg Thieme Verlag Stuttgart.

Electroorganic reactions. Part 56: Anodic oxidation of 2-methyl- and 2-benzylnaphthalenes: Factors influencing competing pathways

A systematic investigation of the anodic oxidation in nucleophilic media of 2-methyl and 2-benzylnaphthalenes, substituted at the 6-position in the naphthalene nucleus and at the 4-phenyl position of the benzylic side chain, has been carried out to identify factors favouring side-chain substitution. Cyclic voltammetry confirms that 6-substitution has a profound effect on the oxidation potentials of the naphthalene nucleus and 13C chemical shifts indicate polar effects at the benzylic carbon. However, little side-chain anodic oxidation is observed under any conditions tried; the radical-cations of electron-rich substrates preferentially dimerise and a strongly electron-withdrawing substituent at the 6-position (EtOSO2) promotes nuclear substitution. In contrast, oxidation with DDQ in aqueous acetic acid gives efficient side-chain oxidation for electron rich substrates, consistent with hydride transfer, possibly intramolecularly via a charge transfer complex.