35675-44-6

Usage

Uses

Used in Pharmaceutical Industry:
P-Tolyl-acetyl chloride is used as a key intermediate for the synthesis of various pharmaceutical drugs, especially those aimed at treating central nervous system disorders. Its role in drug development is pivotal due to its reactivity and ability to form essential drug components.
Used in Agrochemical Industry:
In the agrochemical sector, P-tolyl-acetyl chloride serves as a vital component in the creation of herbicides and insecticides, contributing to the development of effective crop protection agents.
Used in Organic Chemistry:
P-Tolyl-acetyl chloride is utilized as a versatile reagent for the acylation of amines, alcohols, and phenols, which is fundamental in organic chemistry for the preparation of a range of functionalized compounds, expanding its applications beyond the pharmaceutical and agrochemical realms.

InChI:InChI=1/C9H9ClO/c1-7-2-4-8(5-3-7)6-9(10)11/h2-5H,6H2,1H3

Upstream product

• 33155-60-1 t-butyl p-tolylacetate 
• 1206896-65-2 4-(2-chloro-phenyl)-2-methyl-buta-2,3-dienoic acid ethyl ester 
• 622-47-9 4-tolylacetic acid 

Downstream Products

• 92241-60-6 4,4'-[2-(p-tolyl)ethene-1,1-diyl]bis(methoxybenzene) 
• 57297-25-3 1-(4-methoxyphenyl)-2-(4-methylphenyl)ethanone 
• 19715-81-2 N,N-dimethyl-2-(p-tolyl)acetamide 
• 15221-84-8 1-(4-chlorophenyl)-2-(p-tolyl)ethan-1-one 
• 51490-06-3 1,2-di-p-tolyl-ethanone 
• 60312-93-8 4'-methyl-4-phenyl-deoxybenzoin 
• 860571-16-0 4-methoxy-2,4'-dimethyl-deoxybenzoin 
• 118982-60-8 17-(4-methyl-phenethyl)-morphinan-3-ol 
• 21541-97-9 1-(4-methylphenyl)-2-hexanone 
• 95280-69-6 methyl 2-(2-(p-tolyl)acetoxy)benzoate 
• 64267-80-7 p-Tolyl-acetic acid N'-methyl-N'-phenyl-hydrazide 
• 81116-01-0 1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-2-p-tolyl-ethanone 
• 143659-25-0 1-Naphthylmethyl 4-methylphenylacetate 
• 93862-55-6 (S)-4-Isopropyl-3-(2-p-tolyl-acetyl)-oxazolidin-2-one 

Relevant academic research and scientific papers

Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B

A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues

A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.

Identification of BR102910 as a selective fibroblast activation protein (FAP) inhibitor

Fibroblast activation protein (FAP) belongs to the family of prolyl-specific serine proteases and displays both exopeptidase and endopeptidase activities. FAP expression is undetectable in most normal adult tissues, but is greatly upregulated in sites of tissue remodeling, which include fibrosis, inflammation and cancer. Due to its restricted expression pattern and dual enzymatic activities, FAP inhibition is investigated as a therapeutic option for several diseases. In the present study, we described the structure–activity relationship of several synthesized compounds against DPPIV and prolyl oligopeptidase (PREP). In particular, BR102910 (compound 24) showed nanomolar potency and high selectivity. Moreover, the in vivo FAP inhibition study of BR102910 (compound 24) using C57BL/6J mice demonstrated exceptional profiles and satisfactory FAP inhibition efficacy. Based on excellent in vitro and in vivo profiles, the potential of BR102910 (compound 24) as a lead candidate for the treatment of type 2 diabetes is considered.

The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters

Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable.

A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones

Chiral cyclopropane rings are key pharmacophores in pharmaceuticals and bioactive natural products, making libraries of these building blocks a valuable resource for drug discovery and development campaigns. Here, we report the development of a chemoenzymatic strategy for the stereoselective assembly and structural diversification of cyclopropyl ketones, a highly versatile yet underexploited class of functionalized cyclopropanes. An engineered variant of sperm whale myoglobin is shown to enable the highly diastereo- and enantioselective construction of these molecules via olefin cyclopropanation in the presence of a diazoketone carbene donor reagent. This biocatalyst offers a remarkably broad substrate scope, catalyzing this reaction with high stereoselectivity across a variety of vinylarene substrates as well as a range of different α-aryl and α-alkyl diazoketone derivatives. Chemical transformation of these enzymatic products enables further diversification of these molecules to yield a collection of structurally diverse cyclopropane-containing scaffolds in enantiopure form, including core motifs found in drugs and natural products as well as novel structures. This work illustrates the power of combining abiological biocatalysis with chemoenzymatic synthesis for generating collections of optically active scaffolds of high value for medicinal chemistry and drug discovery.

CEPHALOSPORIN CIPROFLOXACIN HYBRID COMPOUNDS

A compound of formula (Ia) and related aspects.

A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides

For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.

N-monoarylacetothioureas as potent urease inhibitors: synthesis, SAR, and biological evaluation

A urease inhibitor with good in vivo profile is considered as an alternative agent for treating infections caused by urease-producing bacteria such as Helicobacter pylori. Here, we report a series of N-monosubstituted thioureas, which act as effective urease inhibitors with very low cytotoxicity. One compound (b19) was evaluated in detail and shows promising features for further development as an agent to treat H. pylori caused diseases. Excellent values for the inhibition of b19 against both extracted urease and urease in intact cell were observed, which shows IC50 values of 0.16 ± 0.05 and 3.86 ± 0.10 μM, being 170- and 44-fold more potent than the clinically used drug AHA, respectively. Docking simulations suggested that the monosubstituted thiourea moiety penetrates urea binding site. In addition, b19 is a rapid and reversible urease inhibitor, and displays nM affinity to urease with very slow dissociation (koff=1.60 × 10?3 s?1) from the catalytic domain.

Palladium-Catalyzed 2-(Neopentylsulfinyl)aniline Directed C–H Acetoxylation and Alkenylation of Arylacetamides

The 2-(neopentylsulfinyl)aniline directing group that promotes rapid palladium-catalyzed C–H acetoxylation and alkenylation of arylacetamides has been developed. The acetoxylation reaches completion within only 40 min at 100 °C and leads to the bis-functionalized products. Alternatively, the reaction can be carried out at room temperature, which is beneficial for sensitive substrates. For the alkenylation, we have developed a protocol in which easily available 1-substituted cyclopropanols were employed as equivalents of vinyl ketones.