4160-52-5

Usage

Uses

Used in Chemical Research:
4-METHYLBUTYROPHENONE is used as a quenching agent for chemically excited acetone phosphorescence. This application is particularly important in the field of chemical research, where the compound helps in studying and understanding the behavior of excited states in chemical reactions.
Used in Analytical Chemistry:
In analytical chemistry, 4-METHYLBUTYROPHENONE serves as a valuable tool for the detection and measurement of acetone phosphorescence. Its ability to quench this phosphorescence allows for more accurate and reliable analysis of samples containing acetone or other related compounds.
Used in Pharmaceutical Industry:
4-METHYLBUTYROPHENONE may also find applications in the pharmaceutical industry, where its unique properties can be utilized in the development of new drugs or drug delivery systems. Its ability to interact with excited states could potentially be harnessed for targeted drug delivery or as a component in drug formulations.
Used in Material Science:
4-METHYLBUTYROPHENONE's ability to quench phosphorescence may also be useful in material science, particularly in the development of new materials with specific optical or electronic properties. 4-METHYLBUTYROPHENONE could be incorporated into the design of advanced materials for various applications, such as sensors, displays, or energy-efficient devices.

InChI:InChI=1/C11H7BrCl2N4O/c12-10-9(5-16-18-11(10)19)17-15-4-6-1-2-7(13)3-8(6)14/h1-5H,(H2,17,18,19)

Upstream product

• 10557-57-0 propylmagnesium iodide 
• 104-85-8 para-methylbenzonitrile 
• 141-75-3 butyryl chloride 
• 108-88-3 toluene 
• 106-31-0 butanoic acid anhydride 
• 107-92-6 butyric acid 
• 7143-76-2 cyclopropyl-p-tolyl-methanone 
• 138354-13-9 C₁₁H₁₂O^(1-) 
• 201230-82-2 carbon monoxide 
• 624-31-7 4-tolyl iodide 
• 107-08-4 1-iodo-propane 
• 24165-63-7 1-p-tolyl-3-buten-1-ol 
• 5142-75-6 tri(p-tolyl)bismuth 
• 994-52-5 butyric acid silicic acid-anhydride 

Downstream Products

• 92321-60-3 2-dimethylaminomethyl-1-p-tolyl-butan-1-one 
• 859080-85-6 1-p-tolyl-butane-1,2-dione-2-oxime 
• 1595-05-7 p-butyltoluene 
• 6282-37-7 1-(4-methylphenyl)butanol 
• 69126-28-9 1-(4-methyl-3-nitrophenyl)-1-butanone 
• 4521-23-7 tolbutamide 
• 4521-22-6 4-(4-methylphenyl)butyric acid 
• 100121-59-3 2-p-toluoyl-butyraldehyde 
• 51089-96-4 1-p-Tolyl-1-butylamin 
• 99-94-5 p-Toluic acid 

Relevant academic research and scientific papers

Rh-Catalyzed Coupling of Aldehydes with Allylboronates Enables Facile Access to Ketones

We present herein a novel strategy for the preparation of ketones from aldehydes and allylic boronic esters. This reaction involves the allylation of aldehydes with allylic boronic esters and the Rh-catalyzed chain-walking of homoallylic alcohols. The key to this successful development is the protodeboronation of alkenyl borylether intermediate via a tetravalent borate anion species in the presence of KHF2 and MeOH. This approach features mild reaction conditions, broad substrate scope, and excellent functional group tolerance. Mechanistic studies also supported that the tandem allylation and chain-walking process were involved.

Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide

The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.

Facile preparation of 5-alkyl-1-aryltetrazoles with arenes, acyl chlorides, hydroxylamine, and diphenylphosphoryl azide

Successive treatment of arenes with acyl chlorides and AlCl3, the addition of water and removal of solvent, the reaction with NH2OH?HCl and K2CO3, and the reaction with diphenylphosphoryl azide and DBU under warming conditions gave the corresponding 5-alkyl-1-aryltetrazoles efficiently in good to moderate yields. The present method is one-pot transformation of arenes into 5-alkyl-1-aryltetrazoles using the Friedel-Crafts acylation and the Beckmann rearrangement under transition-metal-free conditions.

Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy

The discrimination of a fluorine atom from a hydrogen atom has been challenging in asymmetric catalysis. We herein report iridium-catalyzed hydrogenation of α-fluoro ketones using a strategy of dynamic kinetic resolution. Both enantiomeric and diastereomeric selectivities were satisfactory in the preparation of β-fluoro alcohols. The DFT calculation revealed a C-F···Na charge-dipole interaction in the transition state of hydride transfer. This noncovalent interaction would be responsible for the diastereomeric control.

Additive-Free Isomerization of Allylic Alcohols to Ketones with a Cobalt PNP Pincer Catalyst

Catalytic isomerization of allylic alcohols in ethanol as a green solvent was achieved by using air and moisture stable cobalt (II) complexes in the absence of any additives. Under mild conditions, the cobalt PNP pincer complex substituted with phenyl groups on the phosphorus atoms appeared to be the most active. High rates were obtained at 120 °C, even though the addition of one equivalent of base increases the speed of the reaction drastically. Although some evidence was obtained supporting a dehydrogenation–hydrogenation mechanism, it was proven that this is not the major mechanism. Instead, the cobalt hydride complex formed by dehydrogenation of ethanol is capable of double-bond isomerization through alkene insertion–elimination.

Manganese PNP-pincer catalyzed isomerization of allylic/homo-allylic alcohols to ketones-activity, selectivity, efficiency

We report the first manganese catalyzed isomerization of allylic alcohols to produce the corresponding carbonyl compounds. The ligand plays a decisive role in the efficiency of this reaction. Very high conversions could be obtained using a solvent-free reaction system. A detailed DFT study reveals a self-dehydrogenation/hydrogenation reaction mechanism which was verified by the isolation of the α,β-unsaturated ketone as intermediate and a deuterium labeling experiment. It also provided a rationale for the observed selectivity and the higher efficiency of phenyl over isopropyl substitution.

Dirhodium(ii)/P(t-Bu)3 catalyzed tandem reaction of α,β-unsaturated aldehydes with arylboronic acids

Phosphine ligated dirhodium(ii) acetate is advocated as a catalyst for the synthesis of aryl alkyl ketones by the tandem reaction of α,β-unsaturated aromatic or aliphatic aldehydes with arylboronic acids. This tandem procedure included arylation followed by the isomerization reaction. This method exhibits good functional group tolerance and has a broad substrate scope. With the conjugated aldehydes, the one-step synthesis of γ,δ-unsaturated ketones was realized through this reaction. It is noteworthy that the length of the Rh-P bond is an important factor affecting catalytic reactions. The comparative analysis of the crystal structures of axially alkylphosphane and arylphosphane ligated dirhodium(ii) acetate revealed that the shorter Rh-P bond length favors the isomerization process as compared to the longer one. In addition, the dirhodium(ii) compound can be recovered after the completion of the reaction.

Mn/Cu catalyzed addition of arylboronic acid to nitriles: Direct synthesis of arylketones

A direct and efficient synthesis of arylketones via arylboronic acid addition to nitriles in presence of inexpensive Mn/Cu catalytic system is reported. The use of non-precious Mn and Cu salts has been found to be highly advantageous both in terms of accessibility as well as cost effectiveness. A series of arylboronic acids as well as nitriles were used to synthesize a variety of symmetrical and unsymmetrical arylketones. Based on the literature studies, the reaction mechanism is anticipated to go through an aryl radical intermediate which reacted with the copper activated nitrile to give the desired arylketones after the hydrolysis of the imine intermediate.

Palladium-Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones

Alkyl aryl ketones are important structures with applications in many areas of chemistry. Hence, efficient procedures for their production are particularly attractive. In this communication, a general and efficient carbonylative cross-coupling of aryl iodides and unactivated alkyl bromides is presented. By using a simple palladium catalyst, a series of alkyl aryl ketones were synthesized in moderate to excellent yields from readily available alkyl and aryl halides in an In-Ex tube with formic acid as the CO source. In this study both primary and secondary alkyl bromides/iodides were suitable coupling partners. Additionally, this method can also be employed for the late-stage functionalization of complex natural products and polyfunctionalized molecules. (Figure presented.).

Study on the design, synthesis and structure-activity relationships of new thiosemicarbazone compounds as tyrosinase inhibitors

52 Structure-based thiosemicarbazone compounds bearing various substituted-lipophilic part, including substituted-benzaldehyde, substituted-phenylalkan-1-one and their biphenyl-type thiosemicarbazone analogs, were designed, synthesized and evaluated as new tyrosinase inhibitors. The results demonstrated that 22 compounds have potent inhibitory activities against tyrosinase with the IC50 value of lower than 1.0 μM. On the basis of the obtained experimental data, the structure-activity relationships (SARs) were rationally derived. Besides, the inhibition mechanism and the inhibitory kinetics of selected compounds 3d and 6e were investigated, revealing that such type of compounds were belonged to the reversible and competitive tyrosinase inhibitors. To verify the safety of these developed thiosemicarbazone compounds, four randomly selected compounds 3d, 4e, 6a and 9a were also tested in 293T cell line for the evaluation of the cytotoxicity. Interestingly, all these compounds almost did not perform any toxicity to 293T cells even at a high concentration of 1000 μmol/L. Taken together, these results suggested that such compounds could serve as the highly efficient and more safe candidates for the treatment of tyrosinase-related disorders.