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Usage

Uses

Used in Flavor and Fragrance Industry:
2',4'-Dimethylacetophenone is used as a flavoring agent for its sweet chemical, slightly fruity cherry, and powdery coumarin-like aroma characteristics. It is also used as a fragrance ingredient due to its slightly camphoraceous scent with a hint of coconut.
Used in Food Industry:
In the food industry, 2',4'-Dimethylacetophenone is used as a flavor enhancer to impart a unique taste and aroma to various food products. Its sweet and woody notes can add depth and complexity to the flavor profile of dishes.
Used in Beverage Industry:
2',4'-Dimethylacetophenone is utilized in the beverage industry to add a distinct flavor and aroma to alcoholic and non-alcoholic drinks. Its sweet and slightly fruity notes can enhance the taste of beverages, making them more appealing to consumers.
Used in Cosmetics and Personal Care Industry:
In the cosmetics and personal care industry, 2',4'-Dimethylacetophenone is used as a fragrance ingredient in various products such as perfumes, colognes, soaps, and lotions. Its pleasant and versatile scent makes it a popular choice for creating appealing scents in personal care products.
Used in Pharmaceutical Industry:
2',4'-Dimethylacetophenone can be used in the pharmaceutical industry as a starting material for the synthesis of various drugs and medicinal compounds. Its unique chemical properties make it a valuable component in the development of new medications.
Overall, 2',4'-Dimethylacetophenone is a versatile compound with a wide range of applications across different industries, primarily due to its distinct and appealing scent and taste characteristics.

Preparation

By condensation of acetylchloride and m-xylene in the presence of aluminum chloride or in the presence of ferric chloride

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 2974, 1981 DOI: 10.1021/jo00327a028

Upstream product

• 108-24-7 acetic anhydride 
• 108-38-3 m-xylene 
• 64-19-7 acetic acid 
• 56-23-5 tetrachloromethane 
• 75-36-5 acetyl chloride 
• 79-20-9 acetic acid methyl ester 
• 108-88-3 toluene 
• 917-64-6 methyl magnesium iodide 
• 21789-36-6 2,4-dimethylbenzonitrile 
• 88089-31-0 2-(2,4-dimethylphenyl)azirine 
• 85981-82-4 1-(2,4-Dimethylphenyl)-1-methyl-3-phenylpropylhydroperoxid 
• 59877-29-1 1,5-Dimethyl-3,6-bis-trimethylsilanyl-cyclohexa-1,4-diene 
• 26346-85-0 2-bromo-1-(2,4-dimethylphenyl)ethanone 
• 142425-94-3 2,4-dimethylacetophenone oxime 

Downstream Products

• 5466-33-1 2-(2,4-dimethyl-phenyl)-quinoline-4-carboxylic acid 
• 857830-37-6 3-(2,4-dimethyl-phenyl)-3-hydroxy-butyric acid ethyl ester 
• 94054-89-4 1,5-diacetyl-2,4-dimethyl-benzene 
• 84619-24-9 1,6-bis-(2,4-dimethyl-phenyl)-hexane-1,3,4,6-tetraone 
• 7746-54-5 1-(2,4-dimethyl-phenyl)-ethanone-(4-nitro-phenylhydrazone) 
• 100971-98-0 1-(2,4-dimethyl-phenyl)-4-methyl-pentane-1,3-dione 
• 52531-08-5 1-(3-chloromethyl-4,6-dimethyl-phenyl)-ethanone 
• 867134-10-9 [2-(2,4-dimethyl-phenyl)-[4]quinolyl]-phenyl-amine 
• 855761-58-9 [2-(2,4-dimethyl-phenyl)-6-methyl-[4]quinolyl]-p-tolyl-amine 
• 25570-50-7 2-(2,4-dimethyl-phenyl)-3-methyl-but-2-ene 
• 83208-06-4 2-[2.4]xylyl-propanol-⁽²⁾ 
• 1483-60-9 1-(sec-butyl)-2,4-dimethylbenzene 
• 87119-29-7 2-(2,4-dimethyl-phenyl)-decane 
• 33861-07-3 1,1-bis-(2,4-dimethyl-phenyl)-ethene 

Relevant academic research and scientific papers

Pyrazoles: 'one-pot' synthesis from arenes and carboxylic acids

A rapid and efficient method for 'one-pot' synthesis of pyrazoles from (hetero)arenes and carboxylic acids via successive formation of ketones and β-diketones followed by heterocyclization with hydrazine has been developed. The utility of the RCOOH/TfOH/TFAA acylation system for intermediate production of ketones and 1,3-diketones is a key feature of this approach. The preliminary evaluation of the anticancer activity of the synthesized pyrazoles is performed.

Electronic Asymmetry of an Annelated Pyridyl-Mesoionic Carbene Scaffold: Application in Pd(II)-Catalyzed Wacker-Type Oxidation of Olefins

The two donor modules of an annelated pyridyl-mesoionic carbene ligand (aPmic) have different σ- and π-bonding characteristics leading to its electronic asymmetry. A Pd(II) complex 1 featuring aPmic catalyzes the oxidation of a wide range of terminal olefins to the corresponding methyl ketones in good to excellent yields in acetonitrile. The catalytic reaction is proposed to proceed via syn-peroxypalladation and a subsequent rate-limiting 1,2-hydride shift, which is supported by kinetic studies. The electronic asymmetry of aPmic renders a well-defined coordination sphere at Pd. The favored arrangement of reactants on the metal center features an olefin trans to the pyridyl module and a tbutylperoxide trans to the carbene. This arrangement gains added stability by the π-delocalization paved by the compatible orbitals on Pd, the pyridyl module, and the olefin that is perpendicular to the Pd(aPmic) plane. The π-interactions are absent in an alternate arrangement wherein the olefin is trans to the carbene. Density functional theory studies reveal the matching orbital overlaps responsible for the preferred arrangement over the other. This work provides an orbital description for the electronic asymmetry of aPmic.

Isopropanol as a hydrogen source for single atom cobalt-catalyzed Wacker-type oxidation

The first example of a heterogeneous cobalt catalytic system for Wacker-type oxidation catalyzed by a single atom dispersed Co-N/C catalyst using alcohol as the hydrogen source under an oxygen atmosphere is presented. By combining a well-designed, controlled experiment and various methods of characterization, we determined that single atom cobalt was the active center rather than nanoparticle or oxide counterparts.

H2-Generation from Alcohols by the MOF-Based Noble Metal-Free Photocatalyst Ni/CdS/TiO2@MIL-101

The synthesis of important classes of chemical compounds from alcohols helps to conserve Earth's fossil carbon resources, since alcohols can be obtained from indigestible and abundantly available biomass. The utilisation of visible light for the activation of alcohols permits alcohol-based C-N and C-C bond formation under mild conditions inaccessible with thermally operating hydrogen liberation catalysts. Herein, we report on a noble metal-free photocatalyst able to split alcohols into hydrogen and carbonyl compounds under inert gas atmosphere without the requirement of electron donors, additives, or aqueous reaction media. The reusable photocatalyst mediates C-N multiple bond formation using the oxidation of alcohols and subsequent coupling with amines. The photocatalyst consists of a CdS/TiO2 heterojunction decorated with co-catalytic Ni nanoparticles and is prepared on size-optimised colloidal metal-organic framework (MOF) crystallites.

Efficient Palladium(0) supported on reduced graphene oxide for selective oxidation of olefins using graphene oxide as a ‘solid weak acid’

Selective oxidation of olefin derivatives to ketones has made innovative development over palladium(0) supported on reduced graphene oxide. Compared to traditional Wacker oxidation, the novel method offers an economical and environment-friendly option by using graphene oxide (GO) as a ‘solid weak acid’ instead of classical homogeneous catalysts like H2SO4 and CF3COOH. X-ray diffraction, X-ray photoelectron spectroscopy, scanning electron microscope and transmission electron microscopy images of Pd0/RGO showed that the nanoscaled Pd particles generated at the flake structure of reduced graphene oxide. Under optimized condition, up to 44 kinds of ketones with different structures can be prepared with excellent yields.

Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains

Antimicrobial resistance (AMR) is a major health problem worldwide, because of ability of bacteria, fungi and viruses to evade known therapeutic agents used in treatment of infections. Aryldiketo acids (ADK) have shown antimicrobial activity against several resistant strains including Gram-positive Staphylococcus aureus bacteria. Our previous studies revealed that ADK analogues having bulky alkyl group in ortho position on a phenyl ring have up to ten times better activity than norfloxacin against the same strains. Rational modifications of analogues by introduction of hydrophobic substituents on the aromatic ring has led to more than tenfold increase in antibacterial activity against multidrug resistant Gram positive strains. To elucidate a potential mechanism of action for this potentially novel class of antimicrobials, several bacterial enzymes were identified as putative targets according to literature data and pharmacophoric similarity searches for potent ADK analogues. Among the seven bacterial targets chosen, the strongest favorable binding interactions were observed between most active analogue and S. aureus dehydrosqualene synthase and DNA gyrase. Furthermore, the docking results in combination with literature data suggest that these novel molecules could also target several other bacterial enzymes, including prenyl-transferases and methionine aminopeptidase. These results and our statistically significant 3D QSAR model could be used to guide the further design of more potent derivatives as well as in virtual screening for novel antibacterial agents.

P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis

p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.

Acceptorless dehydrogenation and dehydrogenative coupling of alcohols catalysed by protic NHC ruthenium complexes

A new family of protic NHC Ru complexes ligated with a phosphine-tethered imidazole moiety were prepared, which can act as excellent catalysts for acceptorless dehydrogenation of secondary alcohols and dehydrogenative coupling of primary and secondary alcohols, thus leading to the formation of a variety of carbonyl compounds with release of H2.

Selective Oxidation of Styrene Derivatives to Ketones over Palladium(0)/Carbon with Hydrogen Peroxide as the Sole Oxidant

Pd0/C catalyst exhibited excellent catalytic activity in the Wacker oxidation of styrene derivatives to corresponding ketones with hydrogen peroxide as a clean oxidant. Compared with the conventional Wacker system, the newly developed method offers a cost-efficient and environmentally friendly option without the use of a copper salt as a co-catalyst.

Taming of superacids: PVP-triflic acid as an effective solid triflic acid equivalent for Friedel-Crafts hydroxyalkylation and acylation

The application of poly(4-vinylpyridine) supported trifluoromethanesulfonic acid (PVP-TfOH, 1:10) as a convenient solid superacid catalyst system in Friedel-Crafts reactions is described. In the presence of PVP-TfOH, one pot solvent-free synthesis of a wide variety of diarylacetic acid derivatives was achieved by Friedel-Crafts hydroxyalkylation reaction of glyoxylic acid with arenes under mild conditions. Acylation of both activated and deactivated aromatic compounds with acetyl chloride was also achieved using PVP-TfOH complex under solvent-free conditions at room temperature. As the polymer supported triflic acid was found to be a very efficient and an easy-to-handle solid acid, it can be a useful addition to environmentally more adaptable strong acid catalyst systems.