6212-86-8

Usage

Physical appearance

It is a white crystalline solid.

Usage

Commonly used in pharmaceutical and chemical synthesis.

Chemical structure

2-(4-methylphenyl)acetamide is an amide derivative of acetic acid, with a methyl group and phenyl group attached to the nitrogen atom.

Medical properties

Known for its analgesic (pain-relieving) and anti-inflammatory properties.

Pharmaceutical applications

Used in the production of various pharmaceutical drugs.

Synthesis precursor

2-(4-methylphenyl)acetamide has been used as a precursor in the synthesis of other organic compounds.

Handling and storage

It is important to handle and store this chemical with care, as it may be hazardous if not used properly.

InChI:InChI=1/C9H11NO/c1-7-2-4-8(5-3-7)6-9(10)11/h2-5H,6H2,1H3,(H2,10,11)

Upstream product

• 122-00-9 para-methylacetophenone 
• 35675-44-6 4-methylphenylacetyl chloride 
• 104-81-4 4-Methylbenzyl bromide 
• 2947-61-7 (4-methylphenyl)acetonitrile 

Downstream Products

• 91012-04-3 methyl N-(4-methylbenzyl)carbamate 
• 56651-57-1 4-tolylmethyl isocyanate 
• 97426-53-4 2-(p-tolyl)ethanethioamide 
• 39495-97-1 p-tolylmethyl isocyanide 
• 82082-45-9 N-benzyl-2-(4-methylphenyl)acetamide 
• 1372209-58-9 N-methyl-2-(p-tolyl)propanamide 

Relevant academic research and scientific papers

A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.

Ru(ii)- And Ru(iv)-dmso complexes catalyze efficient and selective aqueous-phase nitrile hydration reactions under mild conditions

New water-soluble ruthenium(ii)- and ruthenium(iv)-dmso complexes [RuCl2(dmso)2(NH3)(CH3CN)] (1), [RuCl2(dmso)3(CH3CN)] (2), and [RuCl2(dmso)3(NH3)]·PF6·Cl (3) have been synthesized and characterized using elemental analyses, IR, 1H and 31P NMR, and electronic absorption spectroscopy. The molecular structures of complexes 1-3 were determined crystallographically. The reactivity of complexes 1-3 has been tested for aqueous-phase nitrile hydration at 60 °C in air, and good efficiency and selectivity are shown for the corresponding amide derivatives. Best performance is achieved with complex 3. Amide conversions of 56-99% were obtained with a variety of aromatic, alkyl, and vinyl nitriles. The reaction tolerated hydroxyl, nitro, bromo, formyl, pyridyl, benzyl, alkyl, and olefinic functional groups. Amides were isolated by simple decantation from the aqueous-phase catalyst. A catalyst loading down to 0.0001 mol% was examined and turnover numbers as high as 990?000 were observed. The catalyst was stable for weeks in solution and could be reused more than seven times without significant loss in catalytic activity. The gram-scale reaction was also performed to produce the desired product in high yields. This journal is

Hydration of Aliphatic Nitriles Catalyzed by an Osmium Polyhydride: Evidence for an Alternative Mechanism

The hexahydride OsH6(PiPr3)2 competently catalyzes the hydration of aliphatic nitriles to amides. The main metal species under the catalytic conditions are the trihydride osmium(IV) amidate derivatives OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2, which have been isolated and fully characterized for R = iPr and tBu. The rate of hydration is proportional to the concentrations of the catalyst precursor, nitrile, and water. When these experimental findings and density functional theory calculations are combined, the mechanism of catalysis has been established. Complexes OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2 dissociate the carbonyl group of the chelate to afford κ1-N-amidate derivatives, which coordinate the nitrile. The subsequent attack of an external water molecule to both the C(sp) atom of the nitrile and the N atom of the amidate affords the amide and regenerates the κ1-N-amidate catalysts. The attack is concerted and takes place through a cyclic six-membered transition state, which involves Cnitrile···O-H···Namidate interactions. Before the attack, the free carbonyl group of the κ1-N-amidate ligand fixes the water molecule in the vicinity of the C(sp) atom of the nitrile.

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.

Ruthenium(II) complexes incorporating salicylaldiminato-functionalized N-heterocyclic carbene ligands as efficient and versatile catalysts for hydration of organonitriles

We describe a new synthetic procedure for synthesis of ruthenium(II) complexes containing salicylaldiminato functionalized mixed N-heterocyclic carbene (NHC) ligand and phosphine co-ligand. The complexes (3a-3d) have been obtained in good to excellent yields by transmetalation from the corresponding Ag-NHC complexes (2a-2d) as carbene transfer reagents. All the [Ru-NHC] complexes have been characterized by elemental analyses, spectroscopic methods as well as ESI mass spectrometry. The ligands 1a-1d show their versatility by switching to be O,N,C-chelating in these ruthenium(II) complexes. The resulting complexes have been evaluated as potential catalysts for the selective hydration of nitriles to primary amides, and related amide bond forming reactions, in environmentally friendly medium. The reaction tolerated ether, hydroxyl, nitro, bromo, formyl, pyridyl, benzyl and alkyl functional groups. The catalyst was stable for weeks and could be recovered and reused more than six times without significant loss of activity.

NITRILE HYDRATION CATALYZED BY RECYCLABLE RUTHENIUM COMPLEXES

A method for hydrating a nitrile derivative to generate an amide derivative is provided. The method includes mixing the nitrile derivative with a ruthenium catalyst complex in an aqueous solution to form a mixture, and reacting the nitrile derivative with water in the aqueous solution and in the presence of the ruthenium catalyst complex to form a reacted mixture comprising the amide derivative. The ruthenium catalyst complex is represented by the following structural formula: RuX2(L)n, wherein X is an anionic ligand, L is a bifunctional phosphine ligand, and n is 3 or 4.

Hemilabile β-aminophosphine ligands derived from 1,3,5-triaza-7- phosphaadamantane: Application in aqueous ruthenium catalyzed nitrile hydration

A series of β-aminophosphines derived from 1,3,5-triaza-7- phosphaadamantane (PTA) are described. PTA-CHPhNHPh (1), PTA-CH(p-C 6H4OCH3)NHPh (2), and PTA-CPh2NHPh (3) were prepared in good yield (62-77%) by reaction of lithiated PTA with the corresponding imine followed by hydrolysis. Compounds 1 and 2 were synthesized as pairs of diastereomers which were separated by successive recrystallization from THF/hexane. Compounds 1-3 are somewhat soluble in water (S 25o = 4.8 (1), 4.9 (2), 2.7 (3) g/L). Upon coordination to Ru(II) arene centers both monodentate (κ1-P) [RuCl 2(η6-toluene)(1-3)] and bidentate (κ 2-P,N) [RuCl(η6-toluene)(1-3)]Cl coordination modes were observed. Ru(II) arene complexes 4-6 exhibited hemilabile behavior transitioning between κ1-P and κ2-P,N coordination upon change in solvent or addition of a coordinating ligand such as Cl- or CH3CN. Complexes (4-6) were found to be active air stable catalysts for the aqueous phase hydration of various nitriles with TOF up to 285 h-1 and TON of up to 97 000 observed.

Synthesis of α-Arylcarboxylic acid amides from silyl enol ether via migratory Amidation with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate

α-Arylcarboxylic acid amides were synthesized by reacting silyl enol ethers of aryl ketones and 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP,1). Silyl enol ethers react with ADMP 1 to give N-(α-arylacyl) guanidines via the migration of aryl groups in enol ethers. The products were transformed to the corresponding α-aryl acetamides by treating with LiAlH4.

Aqueous and biphasic nitrile hydration catalyzed by a recyclable Ru(ii) complex under atmospheric conditions

[RuCl2(PTA)4] (PTA = 1,3,5-triaza-7- phosphaadamantane) was found to be a highly active catalyst for aqueous phase nitrile hydration at 100 °C in air. Near quantitative conversion of aromatic, alkyl, and vinyl nitriles to their corresponding amides was observed. The reaction tolerated ether, hydroxyl, nitro, bromo, formyl, pyridyl, benzyl, alkyl, and olefinic functional groups. Some amides were isolated by simple decantation from the aqueous phase catalyst. Catalyst loading down to 0.001 mol% was examined with turnover numbers as high as 22000 observed. The catalyst was stable for weeks in solution and could be reused more than five times without significant loss of activity.

PHENYLTHIOACETIC ACID DERIVATIVES AND USE THEREOF

The invention relates to novel phenylthioacetic acid derivatives of formula (I), to a method for the production thereof, to the use thereof for the treatment and/or prophylaxis of diseases, in addition to the use thereof in the production of medicaments for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prevention of cardiovascular diseases, in particular dyslipidaemia and arteriosclerosis. The compounds act as modulators for the PRAR-alpha receptor.