7774-79-0

Usage

Uses

Used in Insect Attractant Applications:
2-Butanone, 4-(4-methylphenyl)is used as an insect attractant due to its sweet, fruity, floral odor and its ability to attract insects. It has been extensively studied for this purpose and can be utilized in various applications such as pest control and monitoring insect populations.
Used in Flavor and Fragrance Industry:
2-Butanone, 4-(4-methylphenyl)is used as a flavoring agent for its intense, sweet, deep, fruit flavor. It can be incorporated into various food products to enhance their taste and aroma.
Used in Perfumery:
2-Butanone, 4-(4-methylphenyl)is used in the perfumery industry for its sweet, fruity, floral odor. It can be blended with other fragrance components to create unique and appealing scents for perfumes, colognes, and other fragranced products.

Preparation

By condensation of p-tolylaldehyde with acetone followed by hydrogenation.

InChI:InChI=1/C11H14O/c1-9-3-6-11(7-4-9)8-5-10(2)12/h3-4,6-7H,5,8H2,1-2H3

Upstream product

• 33604-67-0 (4-methylphenyl)azo 4-methylphenyl sulfone 
• 78-94-4 methyl vinyl ketone 
• 106-43-4 para-chlorotoluene 
• 106-38-7 para-bromotoluene 
• 297163-75-8 (4-methylphenyl)(ethyl)silanediol 
• 5720-05-8 4-methylphenylboronic acid 
• 598-32-3 2-hydroxy-3-butene 
• 624-31-7 4-tolyl iodide 
• 106-49-0 p-toluidine 
• 4023-84-1 4-(p-tolyl)-3-buten-2-one 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 104-87-0 4-methyl-benzaldehyde 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 57502-37-1 4-(p-tolyl)butan-2-ol 
• 1352441-97-4 1,1-dicyano-2-methyl-4-(4-methylphenyl)-1-butene 
• 78141-21-6 4-(4-methylphenyl)-3-phenyl-2-butanone 
• 3160-38-1 (E)-4-p-tolylbut-3-en-2-one 
• 89538-71-6 1-methyl-3-p-tolyl-propylamine 
• 1381772-17-3 (Z)-1-(4-chlorophenyl)-2-(4-p-tolylbutan-2-ylidene)hydrazine 
• 1381772-14-0 (E)-1-(4-chlorophenyl)-2-(4-p-tolylbutan-2-ylidene)hydrazine 
• 1381772-75-3 1-(4-chlorophenyl)-3-methyl-5-p-tolyl-4,5-dihydro-1H-pyrazole 
• 1381772-51-5 (E)-1-(2-chloro-4-p-tolylbutan-2-yl)-2-(4-chlorophenyl)diazene 
• 14276-95-0 1,1,6-trimethylindan 

Relevant academic research and scientific papers

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study

β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.

Cobalt-Catalyzed Asymmetric 1,4-Reduction of β,β-Dialkyl α,β-Unsaturated Esters with PMHS

A cobalt-catalyzed asymmetric reduction of β,β-dialkyl α,β-unsaturated esters with polymethylhydrosiloxane (PMHS) was reported to deliver the corresponding esters containing a chiral trialkyl carbon center at β-position with up to 97 % yield and 98 % ee. The chiral tridentate ligand oxazoline iminopyridine (OIP) could perform well for the asymmetric reduction instead of chiral bidentate ligands. This operationally simple protocol shows a broad scope of substrates using one equivalent of readily available PMHS as a cheap and easy-to-handle reductive reagent.

Iron powder and tin/tin chloride as new reducing agents of Meerwein arylation reaction with unexpected recycling to anilines

Simple and rapid route for Meerwein arylation reaction using iron powder or a mixture of tin/tin chloride has been developed. In the presence of iron powder, different aryl diazonium salts reacted with methyl vinyl ketone, acrylates, and isopropenyl acetate. Production of oximes was detected as the main product with acrylates or in a mixture with β-aryl methyl ketones in the case of methyl vinyl ketone. The in situ produced HNO2 from an excess of NaNO2/HCl was trapped by alkyl aryl radical to form oximes in the E configuration form. The presence of tin/tin chloride mixture in the reaction of the aryl diazonium salts with methyl vinyl ketone produced Michael products along with β-aryl methyl ketones. The predicted α-aryl methyl ketones from the reaction of isopropenyl acetate with the diazotized anilines were obtained using iron or tin/tin chloride mixture.

Method for carrying out 1,4-conjugate reduction by photochemical catalysis of alpha,beta-ketene compound

The invention belongs to the field of photochemical organic synthesis, and particularly relates to a method for carrying out 1,4-conjugate reduction on an alpha,beta-ketene compound through photochemical catalysis, which comprises the following step: in t

Methanol as hydrogen source: Chemoselective transfer hydrogenation of α,β-unsaturated ketones with a rhodacycle

Methanol is a safe, economic and easy-to-handle hydrogen source. It has rarely been used in transfer hydrogenation reactions, however. We herein report that a cyclometalated rhodium complex, rhodacycle, catalyzes highly chemoselective hydrogenation of α,β-unsaturated ketones with methanol as the hydrogen source. A wide variety of chalcones, styryl methyl ketones and vinyl methyl ketones, including sterically demanding ones, were reduced to the saturated ketones in refluxing methanol in a short reaction time, with no need for inter gas protection, and no reduction of the carbonyl moieties was observed. The catalysis described provides a practically easy and operationally safe method for the reduction of olefinic bonds in α,β-unsaturated ketone compounds.

Palladium Catalysis for Aerobic Oxidation Systems Using Robust Metal–Organic Framework

Described here is a new and viable approach to achieve Pd catalysis for aerobic oxidation systems (AOSs) by circumventing problems associated with both the oxidation and the catalysis through an all-in-one strategy, employing a robust metal–organic framework (MOF). The rational assembly of a PdII catalyst, phenanthroline ligand, and CuII species (electron-transfer mediator) into a MOF facilitates the fast regeneration of the PdII active species, through an enhanced electron transfer from in situ generated Pd0 to CuII, and then CuI to O2, trapped in the framework, thus leading to a 10 times higher turnover number than that of the homogeneous counterpart for Pd-catalyzed desulfitative oxidative coupling reactions. Moreover, the MOF catalyst can be reused five times without losing activity. This work provides the first exploration of using a MOF as a promising platform for the development of Pd catalysis for AOSs with high efficiency, low catalyst loading, and reusability.

Aldehydes as Alkylating Agents for Ketones

Common and non-toxic aldehydes are proposed as reagents for alkylation of ketones instead of carcinogenic alkyl halides. The developed reductive alkylation reaction proceeds in the presence of the commercially available ruthenium catalyst [(cymene)RuCl2]2 (as low as 250 ppm) and carbon monoxide as the reducing agent. The reaction works well for a broad substrate scope, including aromatic and aliphatic aldehydes and ketones. It can be carried out without a solvent and often gives nearly quantitative yields of the products. This straightforward and cost-effective method is promising not only for laboratory application but also for industry, which produces carbon monoxide as a large-scale waste product.

Two efficient pathways for the synthesis of aryl ketones catalyzed by phosphorus-free palladium catalysts

Allylic alcohols, 1-buten-3-ol, 1-penten-3-ol and 1-octen-3-ol, reacted with aryl iodides (iodotoluene, 4-iodotoluene, 4-iodophenol and 4-iodanisole) under Heck reaction conditions to form corresponding saturated aryl ketones in one step. The same products were obtained in a two-step tandem reaction consisted of the Heck coupling of allylic alcohols with aryl iodides, followed by hydrogenation. Reactions were catalyzed by phosphorus-free palladium precursors modified with the menthol-substituted imidazolium chlorides. Formation of crystalline palladium nanoparticles, of the diameter up to 65 nm, in the reaction mixture was evidenced by TEM.

Chiral isoxazolidine-mediated stereoselective umpolung α-phenylation of methyl ketones

An effective asymmetric α-phenylation of methyl ketones with triphenylaluminium in the presence of (+)-benzopyranoisoxazolidine has been developed. The reaction proceeds via the in situ formation of a chiral N-alkoxyenamine and the subsequent diastereoselective nucleophilic phenylation to provide α-phenylated products in moderate to good yields, with high enantioselectivities.

Linear polystyrene-stabilized Rh(III) nanoparticles for oxidative coupling of arylboronic acids with alkenes in water

Linear polystyrene-stabilized Rh(III) nanoparticles (PS-Rh(III)NPs) were obtained when an aqueous solution of RhCl3 was stirred at 90 °C in the presence of KOH, 4-methylphenylboronic acid, and linear polystyrene, as indicated by X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM). PS-Rh(III)NPs exhibited high catalytic activity for the oxidative coupling of arylboronic acids with alkenes. In contrast, PS-Rh(0)NPs prepared with NaBH4 had little activity for the same reaction.