586-37-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxyacetophenone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its chemical structure allows for the creation of a wide range of drugs, making it a valuable component in the development of new medications.
Used in Chemical Synthesis:
In the field of organic chemistry, 3-Methoxyacetophenone is used as a building block for the synthesis of various organic compounds. Its reactivity and functional groups enable chemists to create a diverse array of molecules for research and industrial applications.
Used in Asymmetric Transfer Hydrogenation:
3-Methoxyacetophenone is used as a catalyst in the asymmetric transfer hydrogenation of ketones, a process that is catalyzed by ruthenium(II) complexes. This application is particularly important in the production of enantiomerically pure compounds, which are essential in the pharmaceutical and chemical industries.
Used in Flavor and Fragrance Industry:
Due to its unique chemical properties, 3-Methoxyacetophenone can also be used in the creation of flavors and fragrances. Its ability to impart specific scents and tastes makes it a valuable component in the development of various consumer products, such as perfumes, cosmetics, and food additives.

Synthesis Reference(s)

Journal of the American Chemical Society, 109, p. 7137, 1987 DOI: 10.1021/ja00257a038Synthesis, p. 406, 1987 DOI: 10.1055/s-1987-27965

Flammability and Explosibility

Nonflammable

Upstream product

• 25108-57-0 3-(1-methylethenyl)anisole 
• 89691-63-4 1-(3-methoxy)-phenylethanol 
• 779-81-7 methyl 3-(3-methoxyphenyl)-3-oxopropanoate 
• 141-97-9 ethyl acetoacetate 
• 1711-05-3 m-anisoyl chloride 
• 996-82-7 sodium diethylmalonate 
• 506-82-1 dimethylcadmium 
• 121-71-1 3-Hydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 62924-93-0 N,N-diethyl-3-methoxybenzamide 
• 917-54-4 methyllithium 
• 111790-43-3 N'-[1-(3-Methoxy-phenyl)-eth-(E)-ylidene]-N,N-dimethyl-hydrazine 
• 5000-65-7 2-bromo-3'-methoxyacetophenone 
• 96258-31-0 3,3-(2,2'-biphenyldiyl)-4-methyl-4-(m-methoxyphenyl)-1,2-dioxetane 

Downstream Products

• 855365-08-1 1,5-bis-(3-methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-pentane-1,5-dione 
• 22966-24-1 (E)-1-(3-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 130820-51-8 (2E)-1-(3-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 143613-11-0 2-(3-methyoxyphenyl)-2-methyl-1,3-dioxolane 
• 32904-95-3 4-methoxy-1-phenylbutane-1,3-dione 
• 29681-99-0 m-methoxybenzoylacetone 
• 120125-63-5 cis/trans-ethyl 2-(3-methoxyphenyl)-2-methyl-1-oxirane-1-carboxylate 
• 73582-31-7 ethyl 3-hydroxy-3-(3-methoxyphenyl)butanoate 
• 37730-32-8 (E)-3-(3-methoxyphenyl)but-2-enoic acid 
• 87116-40-3 (2E)-1,3-bis(3-methoxyphenyl)prop-2-en-1-one 
• 25108-57-0 3-(1-methylethenyl)anisole 
• 70597-91-0 1,3-bis(3-methoxyphenyl)propane-1,3-dione 
• 35076-32-5 1-(3'-methoxyphenyl)-3-(N,N-dimethylamino)-1-propanone 
• 94001-64-6 1-(3-methoxy-phenyl)-1-phenyl-ethanol 

Relevant academic research and scientific papers

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

An Artificial Light-Harvesting System with Tunable Fluorescence Color in Aqueous Sodium Dodecyl Sulfonate Micellar Systems for Photochemical Catalysis

In the present work, an artificial light-harvesting system with fluorescence resonance energy transfer (FRET) is successfully fabricated in aqueous sodium dodecyl sulfonate (SDS) micellar systems. Since the tight and orderly arrangement of dodecyl in the SDS micelles is hydrophobic, tetra-(4-pyridylphenyl)ethylene (4PyTPE) can be easily encapsulated into the hydrophobic layer of SDS micelles through noncovalent interaction, which exhibits aggregation-induced emission (AIE) phenomenon and can be used as energy donor. By using amphoteric sulforhodamine 101 (SR101) fluorescent dye attached to the negatively charged surface of SDS micelles through electrostatic interaction as energy acceptor, the light-harvesting FRET process can be efficiently simulated. Through the steady-state emission spectra analysis in the micelle-mediated energy transfer from 4PyTPE to SR101, the fluorescence emission can be tuned and white light emission with CIE coordinates of (0.31, 0.29) can be successfully achieved by tuning the donor/acceptor ratio. More importantly, to better mimic natural photosynthesis, the SDS micelles with 4PyTPE and SR101 FRET system showed enhanced catalytic activity in photochemical catalysis for dehalogenation of α-bromoacetophenone in aqueous solution and the photocatalytic reaction could be extended to gram levels.

Interfacially synthesized 2D COF thin film photocatalyst: efficient photocatalyst for solar formic acid production from CO2and fine chemical synthesis

The targeted synthesis of an efficient, visible light active, recyclable, freestanding covalent organic framework thin film photocatalyst for multi-faceted photocatalysis is the essence of the proposed work. A simple, scalable, reagent free synthesis of a thin film at the interface of 5,10,15,20-tetra-(4-aminophenyl)porphyrin, 2-vinylbenzene-1,4-dicarbaldehyde in nitrobenzene and aqueous glyoxal affords centimetre sized continuous 2D thin film with substantial stability, flexibility and efficient visible light activity. Strikingly different from the regular imine based COF, the incorporation of the glyoxal unit as a modulator helps in band gap tuning and induces flexibility within the thin film. An interplay between time and concentration helps in achieving a thin film photocatalyst with efficient photocatalytic activity for 1,4-NADH regeneration and selective formic acid formation from CO2. The optimum band edge position of the thin film photocatalyst also enables solar fine chemical synthesisviareductive dehalogenation under visible light illumination with excellent recyclability. The present work gives insight into visible light active thin film formation en route to metal-free sustainable photocatalysis.

Luminescent Platinum(II) Complexes with Bidentate Diacetylide Ligands: Structures, Photophysical Properties and Application Studies

A series of platinum(II) complexes supported by terphenyl diacetylide as well as diimine or bis-N-heterocyclic carbene (NHC) ligands have been prepared. The diacetylide ligands adopt a cis coordination mode featuring non-planar terphenyl moieties as revealed by X-ray crystallographic analyses. The electrochemical, photophysical and photochemical properties of these platinum(II) complexes have been investigated. These platinum(II) diimine complexes show broad emission with peak maxima from 566 nm to 706 nm, with two of them having emission quantum yields >60% and lifetimes 2 μs in solutions at room temperature, whereas the platinum(II) diacetylide complexes having bis-N-heterocyclic carbene instead of diimine ligand display photoluminescence with quantum yields of up to 28% in solutions and excited state lifetimes of up to 62 μs at room temperature. Application studies revealed that one of the complexes can catalyze photoinduced aerobic dehydrogenation of alcohols and alkenes, and a relatively non-toxic water-soluble Pt(II) complex displays anti-angiogenic activity.

o-Quinone methide with overcrowded olefin component as a dehydridation catalyst under aerobic photoirradiation conditions

Ano-quinone methide (o-QM) featuring an overcrowded olefinic framework is introduced, which exhibits dehydridation activity owing to its enhanced zwitterionic character, particularly through photoexcitation. The characteristics of thiso-QM enable the operation of dehydridative catalysis in the oxidation of benzylic secondary alcohols under aerobic photoirradiation conditions. An experimental analysis and density functional theory calculations provide mechanistic insights; the ground-state zwitterionic intermediate abstracts a hydride and proton simultaneously, and the active oxygen species facilitate catalyst regeneration.

Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles

Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.

Visible-light photocatalytic selective oxidation of C(sp3)-H bonds by anion-cation dual-metal-site nanoscale localized carbon nitride

Selective oxidation of C(sp3)-H bonds to carbonyl groups by abstracting H with a photoinduced highly active oxygen radical is an effective method used to give high value products. Here, we report a heterogeneous photocatalytic alkanes C-H bonds oxidation method under the irradiation of visible light (λ= 425 nm) at ambient temperature using an anion-cation dual-metal-site modulated carbon nitride. The optimized cation (C) of Fe3+or Ni2+, with an anion (A) of phosphotungstate (PW123?) constitutes the nanoscale dual-metal-site (DMS). With a Fe-PW12dual-metal-site as a model (FePW), we demonstrate a A-C DMS nanoscale localized carbon nitride (A-C/g-C3N4) exhibiting a highly enhanced photocatalytic activity with a high product yield (86% conversion), selectivity (up to 99%), and a wide functional group tolerance (52 examples). The carbon nitride performs the roles of both the visible light response, and improves the selectivity for the oxidation of C(sp3)-H bonds to carbonyl groups, along with the function of A-C DMS in promoting product yield. Mechanistic studies indicate that this reaction follows a radical pathway catalyzed by a photogenerated electron and hole on A-C/g-C3N4that is mediated by thetBuO˙ andtBuOO˙ radicals. Notably, a 10 g scale reaction was successfully achieved for alkane photocatalytic oxidation to the corresponding product with a good yield (80% conversion), and high selectivity (95%) under natural sunlight at ambient temperature. In addition, this A-C/g-C3N4photocatalyst is highly robust and can be reused at least six times and the activity is maintained.

Phase Separation-Promoted Redox Deracemization of Secondary Alcohols over a Supported Dual Catalysts System

Unification of oxidation and reduction in a one-pot deracemization process has great significance in the preparation of enantioenriched organic molecules. However, the intrinsic mutual deactivation of oxidative and reductive catalysts and the extrinsic incompatible reaction conditions are unavoidable challenges in a single operation. To address these two issues, we develop a supported dual catalysts system to overcome these conflicts from incompatibility to compatibility, resulting in an efficient one-pot redox deracemization of secondary alcohols. During this transformation, the TEMPO species onto the outer surface of silica nanoparticles catalyze the oxidation of racemic alcohols to ketones, and the chiral Rh/diamine species in the nanochannels of the thermoresponsive polymer-coated hollow-shell mesoporous silica enable the asymmetric transfer hydrogenation (ATH) of ketones to chiral alcohols. To demonstrate the general feasibility, a series of orthogonal oxidation/ATH cascade reactions are compared to prove the compatible benefits in the elimination of their deactivations and the balance of the cascade directionality. As presented in this study, this redox deracemization process provides various chiral alcohols with enhanced yields and enantioselectivities relative to those from unsupported dual catalysts systems. Furthermore, the dual catalysts can be recycled continuously, making them an attractive feature in the application.

Decatungstate-mediated solar photooxidative cleavage of CC bonds using air as an oxidant in water

With the increasing attention for green chemistry and sustainable development, there has been much interest in searching for greener methods and sources in organic synthesis. However, toxic additives or solvents are inevitably involved in most organic transformations. Herein, we first report the combination of direct utilization of solar energy, air as the oxidant and water as the solvent for the selective cleavage of CC double bonds in aryl olefins. Various α-methyl styrenes, diaryl alkenes as well as terminal styrenes are well tolerated in this green and sustainable strategy and furnished the desired carbonyl products in satisfactory yields. Like heterogeneous catalysis, this homogeneous catalytic system could also be reused and it retains good activity even after repeating three times. Mechanism investigations indicated that both O2- and 1O2 were involved in the reaction. Based on these results, two possible mechanisms, including the electron transfer pathway and the energy transfer pathway, were proposed.

The Reactivity of α-Fluoroketones with PLP Dependent Enzymes: Transaminases as Hydrodefluorinases

A chemical method for the treatment of harmful halogenated compounds that has recently become of interest is the reductive dehalogenation of carbon-halogen bonds. In the case of a fluorine atom, this process is called hydrodefluorination. While many transition metal-based approaches now exist to reductively defluorinate aromatic fluoroarenes, the cleavage of C?F bonds in aliphatic compounds is not so well-developed. Here we propose a biocatalytic approach exploiting a promiscuous activity exhibited by transaminases (TAs). Hence, a series of α-fluoroketones have been defluorinated with excellent conversions using Chromobacterium violaceum and Arthrobacter sp. TAs under mild conditions and in aqueous medium, using a stoichiometric amount of an amine (e. g. 2-propylamine) as reagent and formally releasing its oxidized form (e. g. acetone), with ammonia and hydrogen fluoride as by-products. It is also demonstrated that this process can be performed in a regio- or stereoselective fashion.