30314-42-2

Usage

Uses

Used in Pharmaceutical Industry:
4'-Chloro-2,2-dimethylpropiophenone is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties. Its unique structure allows for the creation of molecules with targeted effects on biological systems.
Used in Agrochemical Industry:
In the agrochemical sector, 4'-chloro-2,2-dimethylpropiophenone serves as an intermediate in the production of agrochemicals, potentially enhancing crop protection and yield through the development of novel pesticides and other agricultural chemicals.
Used in Fragrance Industry:
4'-Chloro-2,2-dimethylpropiophenone is utilized as a component in the creation of fragrance compounds, capitalizing on its chemical structure to produce unique scents for use in perfumes, cosmetics, and other scented products.
Used in Specialty Chemicals Production:
4'-CHLORO-2,2-DIMETHYLPROPIOPHENONE also finds application in the production of specialty chemicals, where its distinctive properties can be harnessed for specific industrial applications, such as in the development of dyes, coatings, or other chemical products that require its particular characteristics.
Used in Research and Development:
4'-Chloro-2,2-dimethylpropiophenone is employed in research settings for the exploration of new chemical reactions and the discovery of novel applications, given its potential to participate in a wide range of organic synthesis processes.

InChI:InChI=1/C11H13ClO/c1-11(2,3)10(13)8-4-6-9(12)7-5-8/h4-7H,1-3H3

Upstream product

• 6200-21-1 (+/-)-2,2-dimethyl-1-(p-chlorophenyl)propan-1-ol 
• 623-03-0 4-Cyanochlorobenzene 
• 677-22-5 tert-butylmagnesium chloride 
• 99-91-2 para-chloroacetophenone 
• 74-88-4 methyl iodide 
• 78132-52-2 4-chlorothiopivalophenone 
• 104-88-1 4-chlorobenzaldehyde 
• 106-39-8 bromochlorobenzene 
• 630-19-3 pivalaldehyde 
• 10364-95-1 1-(4-chloro-benzoyl)-1H-imidazole 
• 84379-72-6 1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate 
• 3282-30-2 pivaloyl chloride 
• 108-90-7 chlorobenzene 
• 17151-48-3 tributyl(4-chlorophenyl)stannane 

Downstream Products

• 31006-79-8 β-p-chlorphenyl-β-tert-butyl-hydracrylsaeure-aethylester 
• 54953-06-9 4-Chlorpivalophenonazin 
• 6200-21-1 (+/-)-2,2-dimethyl-1-(p-chlorophenyl)propan-1-ol 
• 78132-52-2 4-chlorothiopivalophenone 
• 78132-55-5 p-chlorothio-pivalophenone S-oxide 
• 120136-06-3 Toluene-4-sulfonic acid 1-(4-chloro-phenyl)-2,2-dimethyl-propyl ester 
• 114666-01-2 4-chlorophenyl tert.-butyl ketone N-methylhydrazone 
• 1111662-58-8 1-(4-(4-butyl-1-o-tolyl-1H-1,2,3-triazol-5-yl)phenyl)-2,2-dimethylpropan-1-one 
• 86439-94-3 1,2-Bis<1-(4-chlorphenyl)-2,2-dimethylpropyl>hydrazin 
• 68525-44-0 Bis<1-(4-chlorphenyl)-2,2-dimethylpropyl>diazen 
• 170455-86-4 1-(p-ethoxyphenyl)-2,2-dimethyl-1-propanone 

Relevant academic research and scientific papers

Light-DrivenN-Heterocyclic Carbene Catalysis Using Alkylborates

Radical-radical coupling, the selective reaction between two different radical species, has contributed to the methodology for connecting bulky units. Light-drivenN-heterocyclic carbene (NHC) organocatalysis is recognized as a state-of-the-art methodology enabling radical-radical coupling. The catalytic process involves forming an acyl azolium intermediate from the NHC catalyst and an acyl donor, followed by single electron reduction of this key intermediate, which is largely dependent on the photoredox catalyst. We designed a radical NHC catalysis in which the direct photoexcitation of a borate to form a high reducing agent facilitated the single electron reduction event. The borate produces an alkyl radical for the single electron transfer process to accomplish the radical-radical coupling. This protocol enables cross-coupling between alkylborates and acyl imidazoles in addition to radical relay-type alkylacylations of alkenes with alkylborates and acyl imidazoles, affording ketones with a broad scope.

N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes

We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.

Cp?Co(III)-Catalyzed C-H Alkylation with Maleimides Using Weakly Coordinating Carbonyl Directing Groups

A novel protocol for ortho-C-H alkylation of aromatic and heteroaromatic ketones and esters under Cp?Co(III) catalysis has been developed for the first time. The reaction proceeds through initial cyclometalation via weak chelation-assisted C-H bond activation, followed by coordination of activated alkene, insertion between Co-C, and protodemetalation.

Generation of Stable Ruthenium(IV) Ketimido Complexes by Oxidative Addition of Oxime Esters to Ruthenium(II): Reactivity Studies Based on Electronic Properties of the Ru?N Bond

The reaction of an oxime ester with [Ru(PPh3)3X2] proceeded smoothly at room temperature to afford a stable RuIV ketimido complex as oxidative adduct. The structure of the complex was unambiguously determined by X-ray crystallographic analysis, which showed an almost linear Ru?N?C array. The electronic properties of the nitrogen atom were estimated by DFT calculations, and the results suggested double-bond character of the Ru?N bond. Kinetic studies and consideration of the substituent effect on the oxime ester led to the proposal of a reaction mechanism involving oxidative addition, which could proceed by N,O-chelating coordination to the Ru center prior to N?O bond cleavage. The obtained Ru ketimido complex could be transformed into a ruthenacycle by C?H activation by a concerted metalation–deprotonation mechanism in dichloromethane/methanol. Ru ketimido complexes with a tethered alkyne or alkene moiety underwent chloroamination of unsaturated C?C bonds followed by C?H activation, which resulted in the formation of a ruthenacycle. Considering the LUMO of an isolated Ru ketimido complex, the chloroamination should proceed by a synchronous 1,3-dipolar cycloaddition-type mechanism. Insight into the character and reactivity of Ru ketimido complexes will be helpful for developments in the catalytic transformation of oxime esters.

Synergistic interplay of a non-heme iron catalyst and amino acid coligands in H2O2 activation for asymmetric epoxidation of α-alkyl-substituted styrenes

Highly enantioselective epoxidation of α-substituted styrenes with aqueous H2O2 is described by using a chiral iron complex as the catalyst and N-protected amino acids (AAs) as coligands. The amino acids synergistically cooperate with the iron center in promoting an efficient activation of H2O2 to catalyze epoxidation of this challenging class of substrates with good yields and stereoselectivities (up to 97% ee) in short reaction times.

Facile preparation of aromatic ketones from aromatic bromides and arenes with aldehydes

Aromatic ketones were efficiently prepared in good yields by the reactions of aryl bromides with n-BuLi, followed by the reactions with aromatic aldehydes or aliphatic aldehydes and the subsequent treatment with molecular iodine and K2CO3, in a one-pot method. The same treatment of arenes, instead of aromatic bromides, also provided the corresponding aromatic ketones in good yields. Using these methods, various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatics and electron-deficient aromatics could be prepared efficiently by a simple, transition-metal-free, and therefore environmentally benign experimental procedure.

Practical one-pot preparation of ketones from aryl and alkyl bromides with aldehydes and DIH via Grignard reagents

Various diaryl ketones, alkyl aryl ketones, and dialkyl ketones were efficiently prepared in good yields by the reactions of the Grignard reagents derived from aryl or alkyl bromides, followed by the reactions with aromatic or aliphatic aldehydes and the subsequent treatment with 1,3-diiodo-5,5- dimethylhydantoin and K2CO3, in a one-pot method. The same treatment of aromatic bromides bearing electron-withdrawing groups, such as ester, nitrile, ketone, and nitro groups with i-PrMgCl·LiCl or PhMgCl instead of Mg, also provided the corresponding diaryl and alkyl aryl ketones in good yields. The above methods are simple and practical transition-metal-free methods for the preparation of various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatic groups and electron-deficient aromatic groups, as well as dialkyl ketones.

Ultrasound assisted Friedel-Crafts acylation of aromatics using ferric sulphate as catalyst

The use of ultrasound in the acylation reactions of various aromatics and polyaromatics with different acyl chlorides, in the presence of catalytic amount of ferric sulphate at room temperature, gives good yields of the respective ketones with a short reaction time. A facile and simple synthesis of various aromatic ketones using Friedel-Crafts acylation has been established from the corresponding acid chlorides and aromatic or polyaromatic compounds, respectively under mild reaction conditions with shorter reaction times (30-45 min) and in reasonable yields. This method offers the advantage of low cost and ease of purification of the products because of the small amount of ferric sulphate used in these reactions.

Enantioselective hydrogenation and transfer hydrogenation of bulky ketones catalysed by a ruthenium complex of a chiral tridentate ligand

A study on the enantioselective hydrogenation of tertiary alkyl ketones catalysed by a novel class of tridentate-Ru complex is reported. In contrast to the extensively studied [RuCl2(diphos)(di-primary amine)] complexes, this new class of hydro

Practical synthesis of a p38 MAP kinase inhibitor

p38 MAP kinase inhibitors have attracted considerable interest as potential agents for the treatment of inflammatory diseases. Herein, we describe a concise and efficient synthesis of inhibitor 1 that is based on a phthalazine scaffold. Highlights of our approach include a practical synthesis of a 1,6-disubstituted phthalazine building block 24 as well as the one-pot formation of boronic acid 27. Significant synthetic work to understand the reactivity principles of the intermediates helped in selection of the final synthetic route. Subsequent optimization of the individual steps of the final sequence led to a practical synthesisof 1.