5702-74-9

Usage

Uses

Used in Pharmaceutical Industry:
4-ISOPROPYLACETANILIDE is used as an intermediate in the synthesis of acetaminophen (paracetamol), a widely used analgesic and antipyretic drug. Its role in the production of this medication is crucial for managing pain and reducing fever.
Used in Cosmetic and Personal Care Industry:
4-ISOPROPYLACETANILIDE is used as an ingredient in hair and skin care products due to its analgesic and anti-inflammatory properties. It contributes to the effectiveness of these products in providing relief and care for various skin and hair conditions.

InChI:InChI=1/C16H18N2O3/c1-11-14(16(19)17-10-13-8-5-9-20-13)15(18-21-11)12-6-3-2-4-7-12/h2-4,6-7,13H,5,8-10H2,1H3,(H,17,19)

Upstream product

• 99-88-7 4-Isopropylaniline 
• 108-24-7 acetic anhydride 
• 215456-39-6 (-)-cryptone oxime 
• 127-09-3 sodium acetate 
• 1817-47-6 4-nitrocumene 
• 10387-40-3 potassium thioacetate 
• 507-09-5 tiolacetic acid 
• 75-36-5 acetyl chloride 
• 123-54-6 acetylacetone 
• 127-19-5 N,N-dimethyl acetamide 
• 463302-31-0 para-isopropylphenyl isocyanide 
• 2161-86-6 2,4-diacetylphloroglucinol 
• 108-22-5 Isopropenyl acetate 
• 122-79-2 Phenyl acetate 

Downstream Products

• 40655-36-5 N-(4-iso-propyl-2-nitrophenyl)acetamide 
• 91332-83-1 acetic acid-(4-isopropyl-2,6-dinitro-anilide) 
• 68748-07-2 N-<2-bromo-4-(1-methylethyl)phenyl>acetamide 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 874947-55-4 N-Acetyl-N,N-di(4-isopropylphenyl)amine 
• 68701-22-4 2-amino-5-isopropylbenzoic acid 
• 6526-74-5 3-isopropylnitrobenzene 
• 51605-97-1 2-bromo-4-isopropylaniline 
• 63649-64-9 4-isopropyl-2-nitrobenzenamine 
• 400858-42-6 butyl(4-isopropylphenyl)amine 
• 76842-12-1 N-(2-chloro-4-isopropylphenyl)acetamide 
• 328396-72-1 C₁₇H₁₈ClNO 
• 1401456-89-0 2-acetylamino-5-isopropylbenzoic acid ethyl ester 
• 457928-84-6 (S)-3-(3-isopropylphenyl)butanal 

Relevant academic research and scientific papers

Copper-promoted difunctionalization of unactivated alkenes with silanes

An efficient copper-catalyzed cascade difunctionalization of N-allyl anilines toward the synthesis of silylated indolines using commercially available silanes has been reported. This strategy provides a new avenue for the synthesis of a diverse array of i

Magnetically recyclable silica-coated ferrite magnetite-K10montmorillonite nanocatalyst and its applications in O, N, and S-acylation reaction under solvent-free conditions

Novel silica-coated ferrite nanoparticles supported with montmorillonite (K10) have been prepared successfully by using a simple impregnation method. Further, these nanoparticles were characterized by using different analytical methods like FT-IR, PXRD, EDS, and FE-SEM techniques. In addition, these nanoparticles have been explored for their catalytic activity for the O, N, and S-acylation reactions under solvent-free conditions which gave moderate to excellent yields in a much shorter reaction time. Moreover, these nanoparticles could easily be separated out from the reaction medium after the reaction completion by using an external magnetic field and have been re-used for 10 cycles without any significant loss of the catalytic activity.

An organocatalytic C-C bond cleavage approach: A metal-free and peroxide-free facile method for the synthesis of amide derivatives

A facile organocatalytic approach has been devised towards the synthesis of amide derivatives using 1,3-dicarbonyls as easily available acyl-sources under peroxide-free reaction conditions. This transformation was accomplished by the cleavage of the C-C bond in the presence of TEMPO as an organocatalyst and excludes the use of transition-metals and harsh reaction conditions. A broad range of substrates with diverse functional groups were well tolerated and delivered the products in high yields.

Environmentally benign decarboxylative: N-, O-, and S-Acetylations and acylations

An operationally simple and general method for acetylation and acylation of a wide variety of substrates (amines, alcohols, phenols, thiols, and hydrazones) has been reported. Meldrum's acid and its derivatives have been used as an air-stable, non-volatile, cost-effective, and easy to handle acetylating/acylating agent. Easily separable byproducts (CO2 and acetone) allowed the isolation of analytically pure acetylated products without the requirement of work-up and any chromatography. This journal is

An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism

Abstract: Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e. the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans-migration rule of the classical Beckmann rearrangement.

Visible-light-induced Beckmann rearrangement by organic photoredox catalysis

A facile and general strategy for efficient direct conversion of oximes to amides using an inexpensive organic photocatalyst and visible light is described. This radical Beckmann rearrangement can be performed under mild conditions. Various alkyl aryl ketoximes and diaryl ketoximes can be effectively converted into the corresponding amides in excellent yields.

From alkylarenes to anilines via site-directed carbon–carbon amination

Anilines are fundamental motifs in various chemical contexts, and are widely used in the industrial production of fine chemicals, polymers, agrochemicals and pharmaceuticals. A recent development for the synthesis of anilines uses the primary amination of C–H bonds in electron-rich arenes. However, there are limitations to this strategy: the amination of electron-deficient arenes remains a challenging task and the amination of electron-rich arenes has a limited control over regioselectivity—the formation of meta-aminated products is especially difficult. Here we report a site-directed C–C bond primary amination of simple and readily available alkylarenes or benzyl alcohols for the direct and efficient preparation of anilines. This chemistry involves a novel C–C bond transformation and offers a versatile protocol for the synthesis of substituted anilines. The use of O2 as an environmentally benign oxidant is demonstrated, and studies on model compounds suggest that this method may also be used for the depolymerization of lignin.

SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams

A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.

Copper-Catalyzed Site-Selective Oxidative C?C Bond Cleavage of Simple Ketones for the Synthesis of Anilides and Paracetamol

A copper-catalyzed approach for the N-acylation of anilines with acetone and acetophenones via C?C bond cleavage is described. Under the developed conditions both CHCl3 and CH2Cl2 were identified as potential C1-source to promote the transformation. The reaction features a site selective C?C bond cleavage to install the amide moieties with high functional-group compatibility and wide substrate scope. The developed method avoids the use of sensitive and narcotic agents. The method also represents an excellent complement to the previous protocols with lower E-factor (13.91 mg/1 mg) than current industrially used method (E-factor 17.54 mg/1 mg). The developed approach has also been extended for the effective preparation of pyridine derivatives and paracetamol in gram scale. The course of the reaction was monitored by 1H NMR as a preliminary investigation of the reaction mechanism. (Figure presented.).

Werner transition-metal complex (WTMC)-mediated mild and efficient chemo-selective acylation of phenols and anilines under solvent-free condition

Werner-type transition-metal complexes (WTMC) such as [Co(NH3)5Cl]Cl2, Cu[(NH3)4]SO4, Mn(acac)3, Ni[(NH3)6]Cl2, Ni[(en)3]S2O3, and Hg[Co(SCN)4] efficiently promote the chemoselective acetylation of phenols and anilines under solvent-free condition. The results of this study clearly shows that the optimal condition for the acetylation of anilines/phenols (1 mmol) (2a–r) with acetic anhydride (1.2 mmol) in the presence of WTMC (1 mmol) and two drops of H3PO4 on heating for 10 min under solvent-free condition gives the corresponding acetanilides/phenyl acetate (3a–r) in good to excellent yield. Furthermore, the method is simple, efficient, chemoselective, and eco-friendly under solvent-free condition for the acetylation of anilines and phenols promoted by WTMC by using acetic anhydrate as the acetylating agent. The simple preparation of the catalyst, easy procedure of the acetylation reaction, and simple work-up indicate the importance of WTMC for such reactions.