103286-27-7

Usage

Uses

Used in Organic Synthesis:
1-(2-bromo-4-methylphenyl)ethanone is used as a reactant or intermediate for various organic synthesis processes. Its reactivity and the presence of the bromo and methyl groups make it a valuable building block for the creation of more complex molecules.
Used in Pharmaceutical Industry:
1-(2-bromo-4-methylphenyl)ethanone is used as a starting material for the synthesis of pharmaceutical compounds. Its unique structure and reactivity allow for the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
1-(2-bromo-4-methylphenyl)ethanone is used as a research compound in academic and industrial laboratories. Its properties and reactivity are studied to gain insights into the behavior of similar organic compounds and to develop new synthetic methods and strategies.
Used in Material Science:
1-(2-bromo-4-methylphenyl)ethanone is used as a precursor in the development of new materials with specific properties, such as polymers, coatings, or adhesives. Its versatility in organic synthesis enables the creation of materials with tailored characteristics for various applications.

Upstream product

• 591-17-3 meta-bromotoluene 
• 108-24-7 acetic anhydride 
• 7697-27-0 2-bromo-4-methylbenzoic acid 
• 75-16-1 methylmagnesium bromide 
• 947546-75-0 2-bromo-1-ethynyl-4-methylbenzene 
• 824-54-4 2-bromo-4-methylbenzaldehyde 
• 53456-09-0 4-methyl-2-bromobenzoyl chloride 
• 75-36-5 acetyl chloride 

Downstream Products

• 855938-99-7 1-(4-methyl-2-phenoxy-phenyl)-ethanone 
• 24852-84-4 4-methyl-2-(methylthio)acetophenone 
• 874651-69-1 (E)-1-(2-bromo-4-methylphenyl)-3-phenylprop-2-en-1-one 
• 123971-35-7 4-(4-methylphenyl)-2-thiazolecarboxylic acid 
• 129167-74-4 2-bromo-1-(tert-butyl)-4-methylbenzene 
• 14635-91-7 1-methyl-3-(2-phenylethynyl)benzene 

Relevant academic research and scientific papers

Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system

An efficient and sustainable protocol for the hydration of alkynes has been developed under metal/acid/catalyst/ligand-free conditions in a water/ethyl lactate mixture. The hydrogen-bond network in the ethyl lactate and water mixture plays a crucial and decisive role in activating the alkynes for hydration to afford the corresponding methyl ketones. This strategy gives the Markovnikov (ketone) addition product selectively over other possible products. The essential role of hydrogen bonding has been confirmed by experimental and theoretical techniques. A probable mechanism has been suggested by various control tests. The efficacy of the method has been further explored for the competent production of value-added α,β-unsaturated carbonyl compounds through the reaction of aldehydes with alkynes as ketonic surrogates. The environmentally benign hydration method takes place under mild conditions, has broad functional-group compatibility, and uses the ethyl lactate/water (1:3) medium as a “green alternative” in the absence of any hazardous, harmful, or expensive substances.

The intramolecular reaction of acetophenoneN-tosylhydrazone and vinyl: Br?nsted acid-promoted cationic cyclization toward polysubstituted indenes

In the presence of TsNHNH2, a Br?nsted acid-promoted intramolecular cyclization ofo-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydicN-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, whereN-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.

α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles

A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing α-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.

Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids

A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.

Divergent Access to Benzocycles through Copper-Catalyzed Borylative Cyclizations

A copper-catalyzed chemodivergent approach to five- and six-membered benzocycles from dienyl arenes tethered with a ketone has been developed. Through proper choice of coordinating ligands and catalytic conditions, copper-catalyzed borylative cyclization of a single dienyl arene can be diverted to two different pathways, leading to indanols and dihydronaphthalenols with high stereoselectivity. The chiral bidentate bisphosphine ligand (S,S)-Ph-BPE was optimal for asymmetric copper-allyl addition to a tethered ketone via a boat-like transition state, whereas NHC ligands led to boro-allyl addition producing indanols with high diastereoselectivity. (Figure presented.).

Asymmetric Synthesis and Application of Chiral Spirosilabiindanes

Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh-catalyzed asymmetric double hydrosilation, for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on greater than 10 gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh-catalyzed hydrogenation and a Pd-catalyzed intramolecular carboamination.

Acceptorless dehydrogenation of amines and alcohols using simple ruthenium chloride

A highly efficient, economic and environmental friendly catalyst system has been developed for the dehydrogenation of alcohols and amines using simple RuCl3·nH2O and N-benzylhexamethylenetetramine. The in situ catalyst system efficiently oxidized the primary and secondary amines and secondary alcohols into nitrile, imine and ketone products, respectively in moderate to excellent yields. The developed catalyst system was also found to be efficient for the dehydrogenation of N-heterocyles. A detailed mechanism study revealed the first example of N-benzylhexamethylenetetramine (HMTA-Bz) being simultaneously acting as base, reducing agent and hydride source to generate the [Ru(II)(H)2] species as the active catalyst. The mechanism studies also revealed both the alcohol and amine oxidation involves dehydrogenative pathway with the evolution of hydrogen as the only by-product. The developed catalyst system also provides possible platform for the release of hydrogen from liquid organic hydrogen carriers (LOHCs).

Asymmetric Synthesis of 1,2-Dihydronaphthalene-1-ols via Copper-Catalyzed Intramolecular Reductive Cyclization

We describe a copper-catalyzed intramolecular reductive cyclization of easily accessible benz-tethered 1,3-dienes containing a ketone moiety. This process provided biologically active 1,2-dihydronaphthalene-1-ol derivatives in good yields with excellent enantio- and diastereoselectivity. Mechanistic investigations using density functional theory revealed that (Z)- and (E)-allylcopper intermediates formed in situ from the diene and copper catalyst undergo isomerization and selective intramolecular allylation of the (E)-allylcopper form of the major product through a six-membered boatlike transition state. The resulting products were further transformed to fully saturated naphthalene-1-ols by reactions of the olefin moiety.

PdII-Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles

A PdII-catalyzed oxidative tandem cyclization was developed for the construction of fused 5,6-bicyclic N, O-heterocycles. This reaction was enabled by the combined use of a 3-methylpyridine ligand and pentafluorobenzoic acid additive. A range of heterocyclic products with different substituents could be prepared in moderate to good yields via this methodology. Several transformations, including a scaled-up preparation of product 2 a, were also carried out showing the good applicability of our methodology.

One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Br?nsted Acid and Palladium Catalysis

A one-pot catalytic enantioselective allylboration/Mizoroki-Heck reaction of 2-bromoaryl ketones has been developed for the asymmetric synthesis of 3-methyleneindanes bearing a tertiary alcohol center. Br?nsted acid-catalyzed allylboration with a chiral BINOL derivative was followed by a palladium-catalyzed Mizoroki-Heck cyclization, resulting in selective formation of the exo-alkene. This novel protocol provides a concise and scalable approach to 1-alkyl-3-methyleneindan-1-ols in high enantiomeric ratios (up to 96:4 er). The potential of these compounds as chiral building blocks was demonstrated with efficient transformation to optically active diol and amino alcohol scaffolds.