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Cas Database

103-84-4

103-84-4

Identification

  • Product Name:Acetamide,N-phenyl-

  • CAS Number: 103-84-4

  • EINECS:203-150-7

  • Molecular Weight:135.166

  • Molecular Formula: C8H9NO

  • HS Code:29242995

  • Mol File:103-84-4.mol

Synonyms:Acetanilide;Acetanilide(8CI);Acetamidobenzene;Acetanil;Acetylaniline;Antifebrin;Benzenamine, N-acetyl-;N-Acetylaminobenzene;N-Acetylaniline;N-Phenylacetamide;NSC 203231;NSC 7636;Phenalgene;Phenalgin;Antifebrin;acetamide, N-phenyl-;N-Acetylaniline;N-Phenylacetamid;N-phenylacetamide;N-Phénylacétamide;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. SYMPTOMS: Symptoms of exposure to this compound may include contact dermatitis and eczematous skin eruptions; anemia and cyanosis. ACUTE/CHRONIC HAZARDS: This compound is an irritant. It emits toxic fumes when heated to decomposition. Minimum/Potential Fatal Human Dose/BETWEEN 4 & 5/: 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOONFUL & 1 OZ FOR A 70 KG PERSON (150 LB). 5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG, BETWEEN 7 DROPS & 1 TEASPOONFUL FOR 70 KG PERSON (150 LB).Absorption, Distribution and ExcretionIT IS READILY EXCRETED IN THE URINE AS SULFATE OR GLUCURONATE CONJUGATE OF THE PHENOL /N-ACETYL-P-AMINOPHENOL/.

  • Fire-fighting measures: Suitable extinguishing media Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. This chemical is combustible. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Product Description:Acetanilide(Acetylaniline)
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Relevant articles and documentsAll total 916 Articles be found

Optimizing Water Exchange Rates and Rotational Mobility for High-Relaxivity of a Novel Gd-DO3A Derivative Complex Conjugated to Inulin as Macromolecular Contrast Agents for MRI

Granato, Luigi,Vander Elst, Luce,Henoumont, Celine,Muller, Robert N.,Laurent, Sophie

, (2018)

Thanks to the understanding of the relationships between the residence lifetime τM of the coordinated water molecules to macrocyclic Gd-complexes and the rotational mobility τR of these structures, and according to the theory for paramagnetic relaxation, it is now possible to design macromolecular contrast agents with enhanced relaxivities by optimizing these two parameters through ligand structural modification. We succeeded in accelerating the water exchange rate by inducing steric compression around the water binding site, and by removing the amide function from the DOTA-AA ligand [1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid mono(p-aminoanilide)] (L) previously designed. This new ligand 10[2(1-oxo-1-p-propylthioureidophenylpropyl]-1,4,7,10-tetraazacyclodecane-1,4,7-tetraacetic acid (L1) was then covalently conjugated to API [O-(aminopropyl)inulin] to get the complex API-(GdL1)x with intent to slow down the rotational correlation time (τR) of the macromolecular complex. The evaluation of the longitudinal relaxivity at different magnetic fields and the study of the 17O-NMR at variable temperature of the low-molecular-weight compound (GdL1) showed a slight decrease of the τM value (τM310 =?331?ns vs. τM310 =?450?ns for the GdL complex). Consequently to the increase of the size of the API-(GdL1)x complex, the rotational correlation time becomes about 360 times longer compared to the monomeric GdL1 complex (τR?=?33,700?ps), which results in an enhanced proton relaxivity.

Transition metal-free intermolecular a-C-H amination of ethers at room temperature

Buslov, Ivan,Hu, Xile

, p. 3325 - 3330 (2014)

We describe a new method for the intermolecular amination of the α-C-H bonds of ethers. A hypervalent iodine reagent was used as oxidant to enable the amination of cyclic and acyclic alkyl ethers with a wide range of amides, imides, and amines. The amination occurred at room temperature and without a transition metal catalyst. The method could be used to synthesize the anti-cancer prodrug Tegafur and its analogues.

-

Venkataraman,K.,Wagle,D.R.

, p. 3037 - 3040 (1979)

-

Synthesis of 2-(N-cyclicamino)quinoline combined with methyl (E)-3-(2/3/4-aminophenyl)acrylates as potential antiparasitic agents

Bokosi, Fostino R. B.,Beteck, Richard M.,Laming, Dustin,Hoppe, Heinrich C.,Tshiwawa, Tendamudzimu,Khanye, Setshaba D.

, (2021)

A rationally designed series of 2-(N-cyclicamino)quinolines coupled with methyl (E)-3-(2/3/4-aminophenyl)acrylates was synthesized and subjected to in vitro screening bioassays for potential antiplasmodial and antitrypanosomal activities against a chloroquine-sensitive (3D7) strain of Plasmodium falciparum and nagana Trypanosoma brucei brucei 427, respectively. Substituent effects on activity were evaluated; meta-acrylate 24 and the ortho-acrylate 29 exhibited the highest antiplasmodial (IC50 = 1.4 μM) and antitrypanosomal (IC50 = 10.4 μM) activities, respectively. The activity against HeLa cells showed that the synthesized analogs are not cytotoxic at the maximum tested concentration. The ADME (absorption, distribution, metabolism, and excretion) drug-like properties of the synthesized compounds were predicted through the SwissADME software.

-

Hall

, p. 3188 (1964)

-

Synthesis of multilayer polymer-immobilised nanosilver for catalytic study in condensation reaction of aniline and acetylacetone

Basu, Jayanta Kumar,Maji, Nitai Chandra,Sengupta, Sonali,Supriya

, (2020)

Abstract: Silver nanoparticles were synthesized in green route with non-hazardous polyvinyl alcohol and polyvinylpyrrolidone as stabilizing as well as reducing agents and water as green solvent. This silver nanoparticle-embedded polymer composite film, Ag/PVA–PVP was characterized by UV–Vis spectroscopy, SEM and TEM. The catalytic activity of this film was evaluated in reduction of p-nitrophenol, acylation of aniline and synthesis of a β-enaminone, 4-phenylamino-pent-3-en-one with appreciably good results. β-enaminone synthesis reaction was chosen to study the effects of kinetic parameters such as reactant quantity, catalyst loading, solvents and temperatures. In a typical reaction, 89% conversion was achieved. A probable chemical reaction mechanism is suggested. Kinetic model fitting for the synthesis of β-enaminone reaction was done for the first time here. Heterogeneous kinetic model following Eley-Rideal pathway showed an excellent data fitting for the reaction. The rate law parameters were estimated. Graphic abstract: Scheme. Synthesis and catalytic application of multilayer polymer-immobilised nanosilver in condensation reaction of aniline and acetylacetone.[Figure not available: see fulltext.].

Impregnated copper on Fe3O4: an efficient magnetically separable nanocatalyst for rapid and selective acylation of amines

Shokri, Zahra,Zeynizadeh, Behzad

, p. 2467 - 2474 (2017)

The present paper describes the synthesis of N-arylacetamides through acetylation of arylamines with Ac2O in the presence of magnetically recyclable Fe3O4/Cu NPs. All reactions were carried out efficiently in H2O within 2–10?min to give the products in 89–95% yields. Selective acetylation of amines versus alcohols was carried out successfully with this acetylating system. In addition, acetylation of amines and phenols was taken place with the same reactivity. Reusability of the nanocatalyst was examined 5 times without significant loss of its catalytic activity.

METHYLKETENE, A MINOR BUT HIGHLY REACTIVE BYPRODUCT IN THE PYROLYSIS GAS OF ACETONE

Tschamber, Theophile,Streith, Jacques

, p. 4503 - 4506 (1980)

Methylketene was identified during the pyrolysis of acetone, and proved to be much more reactive than ketene: METHYL-β-LACTAMS were the dominant cycloaddition products when imines are reacted with the pyrolysis gas of acetone at ROOM TEMPERATURE.

A binuclear Mn(ii) complex as an efficient catalyst for transamidation of carboxamides with amines

Singh, Divya Pratap,Allam, Bharat Kumar,Singh, Krishna Nand,Singh, Vinod Prasad

, p. 1155 - 1158 (2014)

A binuclear Mn(ii) complex has been synthesized and characterized by different structural methods. The complex contains two unique oxo-bridged metal centres and has been explored as an excellent catalyst for transamidation of carboxamides with amines under solvent-free conditions.

An alternative and facile purification procedure of amidation and esterification reactions using a medium fluorous Mukaiyama reagent

Matsugi, Masato,Suganuma, Misaki,Yoshida, Shoko,Hasebe, Shohei,Kunda, Yoko,Hagihara, Kotaro,Oka, Sayaka

, p. 6573 - 6574 (2008)

A convenient methodology for the separation of a fluorous by-product using fluorous chemistry is described. A Mukaiyama coupling reagent bearing a medium fluorous tag, between 40% and 60% fluorine by weight, can be effectively separated from non-fluorous components by increasing the water content of the crude reaction mixture and subsequent filtration. Additional fluorous solid phase extraction is not necessary.

Harnessing the pyrroloquinoxaline scaffold for FAAH and MAGL interaction: Definition of the structural determinants for enzyme inhibition

Brindisi, Margherita,Brogi, Simone,Maramai, Samuele,Grillo, Alessandro,Borrelli, Giuseppe,Butini, Stefania,Novellino, Ettore,Allarà, Marco,Ligresti, Alessia,Campiani, Giuseppe,Di Marzo, Vincenzo,Gemma, Sandra

, p. 64651 - 64664 (2016)

This paper describes the development of piperazine and 4-aminopiperidine carboxamides/carbamates supported on a pharmacogenic pyrroloquinoxaline scaffold as inhibitors of the endocannabinoid catabolizing enzymes fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL). Structure-activity relationships and molecular modelling studies allowed the definition of the structural requirements for dual FAAH/MAGL inhibition and led to the identification of a small set of derivatives (compounds 5e, i, k, m) displaying a balanced inhibitory profile against both enzymes, with compound 5m being the frontrunner of the subset. Favorable calculated physico-chemical properties suggest further investigation for specific analogues.

Preparation, characterization and application of RHA/TiO2 nanocomposites in the acetylation of alcohols, phenols and amines

Seddighi, Mohadeseh,Shirini, Farhad,Goli-Jolodar, Omid

, p. 1003 - 1010 (2016)

In this work, anatase-phase nano-titania was prepared by embedding in rice husk ash, and identified using a variety of techniques. The obtained nanocomposite (RHA/TiO2) was used as a green and inexpensive catalyst for the promotion of the acetylation of alcohols, phenols and amines with Ac2O at room temperature under solvent free conditions. The procedure gave the products in excellent yields during all reaction times. Also this catalyst can be reused for several times without loss of its catalytic activity.

-

Soloway,Friess

, p. 5000 (1951)

-

Additive-free chemoselective acylation of amines and thiols

Mojtahedi, Mohammad M.,Saeed Abaee,Heravi, Majid M.,Behbahani, Farahnaz K.

, p. 95 - 99 (2007)

Amines with different stereoelectronic nature were efficiently acylated at room temperature using acetic anhydride in the presence of no solvent or additive. Various thiols also react equally well under the same conditions. Chemoselective protection of amines in the presence of thiols, alcohols, and phenols and of thiols in the presence of alcohols, and phenols were achieved using competitive experiments.

-

Kenner,Stedman

, p. 2069,2075 (1952)

-

Beckmann rearrangement: Thiamine hydrochloride as a remarkable catalyst for one-pot synthesis of amides from ketones

Mahajan, Sheena,Slathia, Nancy,Kapoor, Kamal K.

, (2020)

Thiamine hydrochloride catalyzed synthesis of amides from ketones including 3-acetyl coumarin via Beckmann rearrangement has been reported. The reaction is believed to involve oxime formation, cleavage of C[sbnd]C bond followed by C[sbnd]N bond formation in one-pot. Thiamine hydrochloride is stable, cheap, easy to handle and environmentally friendly.

-

Cohen,Harrison

, p. 1060 (1897)

-

A simple and practical halogenation of activated arenes using potassium halide and oxone in water-acetonitrile medium

Tamhankar,Desai,Mane,Wadgaonkar,Bedekar

, p. 2021 - 2027 (2001)

A simple and practical halogenation of activated arenes using a reagent combination of potassium halide and oxone in water-acetonitrile medium is presented. The halogenated products were obtained with good yields and in high purity.

The effect of flavonoid aglycones on the CYP1A2, CYP2A6, CYP2C8 and CYP2D6 enzymes activity

Boji?, Mirza,Kond?a, Martin,Rimac, Hrvoje,Benkovi?, Goran,Male?, ?eljan

, (2019)

Cytochromes P450 are major metabolic enzymes involved in the biotransformation of xenobiotics. The majority of xenobiotics are metabolized in the liver, in which the highest levels of cytochromes P450 are expressed. Flavonoids are natural compounds to which humans are exposed through everyday diet. In the previous study, selected flavonoid aglycones showed inhibition of CYP3A4 enzyme. Thus, the objective of this study was to determine if these flavonoids inhibit metabolic activity of CYP1A2, CYP2A6, CYP2C8, and CYP2D6 enzymes. For this purpose, the O-deethylation reaction of phenacetin was used for monitoring CYP1A2 enzyme activity, coumarin 7-hydroxylation for CYP2A6 enzyme activity, 6-α-hydroxylation of paclitaxel for CYP2C8 enzyme activity, and dextromethorphan O-demethylation for CYP2D6 enzyme activity. The generated metabolites were monitored by high-performance liquid chromatography coupled with diode array detection. Hesperetin, pinocembrin, chrysin, isorhamnetin, and morin inhibited CYP1A2 activity; apigenin, tangeretin, galangin, and isorhamnetin inhibited CYP2A6 activity; and chrysin, chrysin-dimethylether, and galangin inhibited CYP2C8. None of the analyzed flavonoids showed inhibition of CYP2D6. The flavonoids in this study were mainly reversible inhibitors of CYP1A2 and CYP2A6, while the inhibition of CYP2C8 was of mixed type (reversible and irreversible). The most prominent reversible inhibitor of CYP1A2 was chrysin, and this was confirmed by the docking study.

Synthesis of acetamides from aryl amines and acetonitrile by diazotization under metal-free conditions

Duan, Pan,Guo, Yu,Kang, Huan,Li, Yi-Na,Wen, Xianghao,Xiao, Fang,Zeng, Yao-Fu,Zhang, Na-Na

, p. 2169 - 2172 (2019)

An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.

Ruthenium(III) acetylacetonate [Ru(acac)3] -An efficient recyclable catalyst for the acetylation of phenols, alcohols, and amines under neat conditions

Varala, Ravi,Nasreen, Aayesha,Adapa, Srinivas R.

, p. 148 - 152 (2007)

A catalytic amount of ruthenium(III) acetylacetonate (2 mol%) [Ru(acac)3] enables solvent-free acetylation of phenols, alcohols, and amines at ambient temperature in good to excellent yields. Furthermore, the catalyst could be recovered and reused at least three times without a significant loss in yields.

Ipso-amidation of arylboronic acids: Xenon difluoride-nitriles as efficient reagent systems

Prakash, G.K. Surya,Moran, Matthew D.,Mathew, Thomas,Olah, George A.

, p. 806 - 809 (2009)

The xenon difluoride-mediated, ipso-amidation of boronic acids has been achieved for the first time under mild conditions. This method provides a simple, one-pot procedure for the direct synthesis of a series of anilides from the corresponding arylboronic

-

Tanaka

, p. 213,214 (1970)

-

Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino) Acetate (ortho-NosylOXY)-Mediated Double Beckmann Rearrangement of Ketoximes under Microwave Irradiation: A Mechanistic Perception

Dev, Dharm,Kalita, Tapasi,Mondal, Tanmay,Mandal, Bhubaneswar

, p. 1427 - 1435 (2021)

A method for Beckmann rearrangement using ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino) acetate (o-NosylOXY) under microwave irradiation is reported. Ketoximes (19 examples) are converted to the corresponding amides/lactams with 69–97% yields in ~10 minutes without any Lewis acid or co-catalyst. This is an example of halogen-free organocatalytic Beckmann rearrangement. Nuclear magnetic resonance (NMR)- and high-resolution mass spectrometry (HRMS)-based detailed mechanistic investigation suggest that o-NosylOXY acts as an initiator. Such initiators are reported before based on density functional theory (DFT) calculations. However, we report here the HRMS signatures of two transient intermediates, the nitrilium ion and the nitrilium ion's dimeric species. Rigorous NMR-based investigation of the reaction mechanism is performed. Our results indicate that the reported Beckmann rearrangement proceeds via two consecutive rearrangements. (Figure presented.).

Eco-friendly reductive acetamidation of arylnitro compounds by thioacetate anion through in situ catalytic regeneration: application in the synthesis of Acetaminophen

Bhattacharya, Apurba,Suarez, Victor,Tamez Jr., Victoriano,Wu, Jiejun

, p. 3221 - 3223 (2006)

A novel one-step reductive acetamidation of arylnitro compounds mediated by thioacetate anion in thioacetic acid via in situ catalytic regeneration was developed and applied to an efficient synthesis of Acetaminophen.

Immobilization of Candida cylindracea lipase on poly lactic acid, polyvinyl alcohol and chitosan based ternary blend film: Characterization, activity, stability and its application for N-a

Badgujar, Kirtikumar C.,Dhake, Kishor P.,Bhanage, Bhalchandra M.

, p. 1335 - 1347 (2013)

The ecofriendly ternary blend polymer film was prepared from the chitosan (CH), polylactic acid (PLA) and polyvinyl alcohol (PVA). Immobilization of Candida cylindracea lipase (CCL) was carried out on ternary blend polymer via entrapment methodology. The ternary blend polymer and immobilized biocatalyst were characterized by using N2 adsorption-desorption isotherm, SEM, FTIR, DSC, and (%) water content analysis through Karl Fischer technique. Biocatalyst was then subjected for the determination of practical immobilization yield, protein loading and specific activity. Immobilized biocatalyst was further applied for the determination of biocatalytic activity for N-acylation reactions. Various reaction parameters were studied such as effect of immobilization support (ratio of PLA:PVA:CH), molar ratio (dibutylamine:vinyl acetate), solvent, biocatalyst loading, time, temperature, and orbital speed rotation. The developed protocol was then applied for the N-acylation reactions to synthesize several industrially important acetamides with excellent yields. Interestingly, immobilized lipase showed fivefold higher catalytic activity and better thermal stability than the crude extract lipase CCL. Furthermore various kinetic and thermodynamic parameters were studied and the biocatalyst was efficiently recycled for four successive reuses. It is noteworthy to mention that immobilized biocatalyst was stable for period of 300 days.

Selective N-acetylation of aromatic amines using acetonitrile as acylating agent

Saikia, Ujwal Pratim,Hussain, Farhaz L.,Suri, Mrinaly,Pahari, Pallab

, p. 1158 - 1160 (2016)

A method for N-acetylation of amines has been developed using acetonitrile as an acylating agent and in situ generated trimethylsilyl iodide as the catalyst under microwave heating condition. The reaction is selective toward aromatic amines while aliphatic amines remain intact. The process eliminates the requirement of toxic acylating reagents like acetic anhydride and acetyl chloride.

-

Yamashita et al.

, p. 1585 (1976)

-

1,2-Diethoxyethane catalyzed oxidative cleavage of gem-disubstituted aromatic alkenes to ketones under minimal solvent conditions

Liu, Kai-Jian,Deng, Ji-Hui,Zeng, Tang-Yu,Chen, Xin-Jie,Huang, Ying,Cao, Zhong,Lin, Ying-Wu,He, Wei-Min

, p. 1868 - 1872 (2020)

Aerobic oxidation using pure dioxygen gas as the oxidant has attracted much attention, but its application in synthetic chemistry has been significantly hampered by the complexity of catalytic system and potential risk of high-energy dioxygen gas. By employing 1,2-diethoxyethane as a catalyst and ambient air as an oxidant, an efficient protocol for the construction of various aryl-alkyl and diaryl ketones through oxidative cleavage of gem-disubstituted aromatic alkenes under minimal solvent conditions has been achieved.

A New, Convenient Method for Semmler-Wolff Aromatization

Tamura, Yasumitsu,Yoshimoto, Yoshihiko,Sakai, Kiyoshi,Kita, Yasuyuki

, p. 483 - 484 (1980)

-

Activation of Superoxide; Efficient Desulphurization of Thioamides to the Corresponding Amides using a Peroxyphosphorus Intermediate generated from Phenylphosphonic Dichloride and Superoxide

Kim, Yong Hae,Lim, Sang Chul,Chang, Hae Sung

, p. 36 - 37 (1990)

Treatment of thioamides with a peroxyphosphorus intermediate generated from phenylphosphonic dichloride and superoxide (O2-radical-anion) at -4 deg C in acetonitrile gave the corresponding amides in excellent yields.

Direct amide formation in a continuous-flow system mediated by carbon disulfide

Orsy, Gy?rgy,Fül?p, Ferenc,Mándity, István M.

, p. 7814 - 7818 (2020)

Amide bonds are ubiquitous in nature. They can be found in proteins, peptides, alkaloids, etc. and they are used in various synthetic drugs too. Amide bonds are mainly made by the use of (i) hazardous carboxylic acid derivatives or (ii) expensive coupling agents. Both ways make the synthetic technology less atom economic. We report a direct flow-based synthesis of amides. The developed approach is prominently simple and various aliphatic and aromatic amides were synthetized with excellent yields. The reaction in itself is carried out in acetonitrile, which is considered as a less problematic dipolar aprotic solvent. The used coupling agent, carbon disulfide, is widely available and has a low price. The utilized heterogeneous Lewis acid, alumina, is a sustainable material and it can be utilized multiple times. The technology is considerably robust and shows excellent reusability and easy scale-up is carried out without the need of any intensive purification protocols.

Convenient, cost-effective, and mild method for the N-acetylation of anilines and secondary amines

Prasad,Srinivasa,Channe Gowda

, p. 1189 - 1195 (2005)

An efficient, cost-effective, and mild method for the N-acetylation of anilines and secondary amines with ammonium acetate in acetic acid media at reflux temperature in good yield is described. Copyright Taylor & Francis, Inc.

Solid supported microwave-assisted Beckmann rearrangement of ketoximes in dry media

Matloubi Moghaddam, Firouz,Rad, Abbas Ali Rastegar,Zali-Boinee, Hassan

, p. 2071 - 2075 (2004)

An AlCl3-ZnCl2 mixture supported on silica gel is found to be a new efficient medium for the Beckmann rearrangement in solvent-free conditions under microwave irradiation. The yields are good to excellent.

Acyl transfer catalysis with 1,2,4-Triazole anion

Yang, Xing,Birman, Vladimir B.

, p. 1499 - 1502 (2009)

1,2,4-Triazole anion has been identified as an active acyl transfer catalyst suitable for the aminolysis and transesterification of esters.

AIBN-promoted amidation of anilines with 1, 3-diketones via oxidative cleavage of C–C bond under aerobic conditions

Rao, Sadu Nageswara,Mohan, Darapaneni Chandra,Adimurthy, Subbarayappa

, p. 4889 - 4894 (2016)

N-Acylation of anilines with 1, 3-diketones promoted by AIBN (2-2′-azoisobutyronitrile) under metal-free and peroxide-free conditions in the presence of molecular oxygen as oxidant has been described. This protocol proceeds by the oxidative cleavage of C–C bond with simultaneous intermolecular C–N bond formation under mild conditions.

Cyanuric chloride catalyzed Beckmann rearrangement of ketoximes in biodegradable ionic liquids

Maia, Angelamaria,Albanese, Domenico C.M.,Landini, Dario

, p. 1947 - 1950 (2012)

Imidazolium-based ionic liquids (ILs) containing ester moieties in the side chain were successfully used as an alternative to traditional ILs in the Beckmann rearrangement of ketoximes catalyzed by 2,4,6-trichloro[1,3,5]triazine. The procedure is mild and suitable for both aromatic and cycloaliphatic substrates affording the rearrangement products in good to quantitative yields. The process is eco-sustainable since these ILs are biodegradable and in addition they can be recovered and reused.

Beckmann rearrangement of ketoximes to lactams by triphosphazene catalyst

Hashimoto, Masaharu,Obora, Yasushi,Sakaguchi, Satoshi,Ishii, Yasutaka

, p. 2894 - 2897 (2008)

(Chemical Equation Presented) Triphosphazene, 1,3,5-triazo-2,4,6- triphosphorine-2,2,4,4,6,6-chloride (TAPC), was found to be an efficient catalyst for the Beckmann rearrangement of cyclohexanone oxime and cyclododecanone oxime to ε-caprolactam and laurolactam, which are raw materials of nylon-6 and nylon-12, respectively.

Beckmann rearrangement of O-4-pentenyl oxime through N- bromosuccinimide-mediated activating process

Kitagawa, Osamu,Fujita, Masao,Okada, Midori,Taguchi, Takeo

, p. 32 - 35 (1997)

Beckmann rearrangement of O-4-pentenyl oxime derivatives proceeds in good yield under mild conditions through the formation of a cationic tetrahydrofuranium intermediate in the halocyclization reaction with N- bromosuccinimide.

A magnetically recoverable copper–salen complex as a nano-catalytic system for amine protection via acetylation using thioacetic acid

Yazdani, Elahe,Kazemi Miraki, Maryam,Salamatmanesh, Arefe,Azarnia, Jamshid,Azizi, Kobra,Ghandi, Leila,Heydari, Akbar

, p. 1775 - 1793 (2019)

A novel copper(II)–salen complex was immobilized on the surface of magnetite nanoparticles using chitosan as a linker. This system exhibits superior catalytic activity in acetyl protection of various amines with thioacetic acid as the acetylating reagent. The method has advantages over others in high selectivity, simple work-up, green reaction medium and the application of an easily recoverable heterogeneous catalyst.

The ortho-substituted N,N-diacetylaniline as a selective acetylating reagent

Murakami, Yasuoki,Kondo, Kazuhiro,Miki, Kazuki,Akiyama, Yoko,Watanabe, Toshiko,Yokoyama, Yuusaku

, p. 3751 - 3754 (1997)

Selective acetylation of the less hindered amino group in the presence of the more hindered amino group with the use of 2-trifluoromethyl-N,N-diacetylaniline 2c is described. This acetylation with 2c yielded the corresponding less hindered monoacetamide exclusively, simply, conveniently, and in good yields.

Beckmann rearrangement of ketoximes on solid metaboric acid: A simple and effective procedure

Chandrasekhar, Sosale,Gopalaiah, Kovuru

, p. 2455 - 2457 (2002)

When ketoximes admixed with solid metaboric acid (formed from boric acid at 100°C/0.1 Torr) are heated (~140°C/7-42 h), the corresponding amides or lactams are produced in excellent yields (62-92%) via the Beckmann reaction. Aromatic aldoximes undergo both dehydration to the nitrile as well as (non-stereospecific) rearrangement under the above conditions. The absence of solvent, and the mildness and low toxicity of boric acid, characterise the present procedure.

Indium mediated reductive acylations of nitroarenes towards N,O-diacylated N-arylhydroxylamines

Kim,Jae Wook Cheong,Han,Jun,Baik,Lee

, p. 3577 - 3586 (2001)

By applying indium, Ac2O, MeOH, and catalytic amount of InCl3 in CHCl3 solution, nitroarenes were transformed into N,O-diacylated N-arylhydroxylamines in moderate to excellent yields.

Synthesis of N,O-Diacetylated N-Arylhydroxylamines by Reduction of Nitroaromatics with Zinc and Acetic Anhydride

Kim, Byeong Hyo,Jun, Young Moo,Suh, Seung Won,Baik, Woonphil,Lee, Byung Min

, p. 46 - 47 (1998)

Reduction of nitroaromatic compounds with zinc and acetic anhydride in dichloromethane gave N,O-diacetylated N-arylhydroxylamines in good yields under mild conditions.

Iterative C?H Functionalization Leading to Multiple Amidations of Anilides

Park, Juhyeon,Lee, Jia,Chang, Sukbok

, p. 4256 - 4260 (2017)

Polyaminobenzenes were synthesized by the ruthenium-catalyzed iterative C?H amidation of anilides using dioxazolones as an amino source. This strategy could be implemented by the sequential activation of C?H bonds of formerly generated compounds by cascade chelation assistance of newly installed amide groups. Computational studies provided a rationale.

Unexpected results from the re-investigation of the Beckmann rearrangement of ketoximes into amides by using TsCl

Pi, Hong-Jun,Dong, Jin-Dong,An, Na,Du, Wenting,Deng, Wei-Ping

, p. 7790 - 7793 (2009)

TsCl (p-toluenesulfonyl chloride), a commercially available organosulfonyl chloride, has been widely used as a stoichiometric dehydrogenation reagent in the transformation of ketoximes into corresponding amides via the Beckmann rearrangement. It has been now found to catalyze the Beckmann rearrangement with high catalytic efficiency, converting a wide range of ketoximes into their corresponding amides under mild condition with good to excellent yields (up to 99% of yield with 1-5 mol % of catalyst loading).

Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media

Verma, Saumya,Kumar, Puneet,Khatana, Anil K.,Chandra, Dinesh,Yadav, Ajay K.,Tiwari, Bhoopendra,Jat, Jawahar L.

, p. 3272 - 3276 (2020)

A zinc(II)-catalyzed single-step protocol for the Beckmann rearrangement using hydroxylamine-O-sulfonic acid (HOSA) as the nitrogen source in water was developed. This direct method efficiently produces secondary amides under open atmosphere in a pure form after basic aqueous workup. It isenvironmentally benign and operationally simple.

Chitosan supported Zn(II) mixed ligand complexes as heterogeneous catalysts for one-pot synthesis of amides from ketones via Beckmann rearrangement

Anuradha,Kumari, Shweta,Layek, Samaresh,Pathak, Devendra D.

, p. 368 - 373 (2017)

Chitosan supported Zn(II) mixed ligand complexes have been synthesized and characterized by FT-IR, UV–Vis, TGA, XRD, FESEM, EDX, AAS and Elemental Analysis. These complexes have been found to be efficient and recyclable heterogeneous catalysts for the one-pot synthesis of amides via Beckmann rearrangement. All three complexes can be easily filtered out from the reaction medium and reused up to five times without significant loss of catalytic activity. The reported protocol is economical and novel in the sense that amides can be easily synthesized in only one-step. All products were obtained as white to off-white crystalline solids and fully characterized by 1H NMR, FT-IR and Mass Spectra.

-

Horino,Inoue

, p. 2403 (1979)

-

One-pot synthesis of spiropyrroloquinoline-isoindolinone and their aza-analogs via the Ugi-4CR/metal-free intramolecular bis-annulation process

Ghandi, Mehdi,Zarezadeh, Nahid,Abbasi, Alireza

, p. 8211 - 8220 (2015)

This presentation discloses a one-pot synthesis of a series of spiropyrroloquinoline isoindolinone and spiropyrroloquinoline aza-isoindolinone scaffolds. The reaction proceeds by the combination of a Ugi four-component reaction (4CR) and two intramolecular cyclizations under metal-free conditions. The proof of the structures relies on analytical investigation and X-ray crystallography.

Noncross-linked polystyrene nanoencapsulation of ferric chloride: A novel and reusable heterogeneous macromolecular Lewis acid catalyst toward selective acetylation of alcohols, phenols, amines, and thiols

Alinejad, Sara,Donyapeyma, Ghazaleh,Rahmatpour, Ali

, (2022/01/24)

Ferric chloride has been successfully nanoencapsulated for the first time on a non-cross-linked polystyrene matrix as the shell material via the coacervation technique. The resulting polystyrene nanoencapsulated ferric chloride was used as a novel and rec

Protodesilylation of Arylsilanes by Visible-Light Photocatalysis

García Manche?o, Olga,Kuhlmann, Jan H.,Uygur, Mustafa

supporting information, p. 1689 - 1694 (2022/03/14)

The first visible-light-mediated photocatalytic, metal- and base-free protodesilylation of arylsilanes is presented. The C(sp2)-Si bond cleavage process is catalyzed by a 5 mol % loading of a commercially available acridinium salt upon blue-light irradiation. Two simple approaches have been identified employing either aerobic or hydrogen atom transfer cocatalytic conditions, which enable the efficient and selective desilylation of a broad variety of simple and complex arylsilanes under mild conditions.

Pd-Catalysed oxidative carbonylation of α-amino amides to hydantoins under mild conditions

Botla, Vinayak,Carfagna, Carla,Della Ca, Nicola,Gabriele, Bartolo,Maestri, Giovanni,Mancuso, Raffaella,Montanari, Luca,Motti, Elena,Voronov, Aleksandr

, p. 294 - 297 (2022/01/06)

The first example of palladium-catalysed oxidative carbonylation of unprotected α-amino amides to hydantoins is described here. The selective synthesis of the target compounds was achieved under mild conditions (1 atm of CO), without ligands and bases. The catalytic system overrode the common reaction pathway that usually leads instead to the formation of symmetrical ureas.

Solvent-free, Efficient Transamidation of Carboxamides with Amines Catalyzed by Recyclable Sulfated Polyborate Catalyst

Mali, Anil S.,Indalkar, Krishna,Chaturbhuj, Ganesh U.

, p. 369 - 378 (2021/07/26)

-

Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd&at;MCP) for chemoselective N-formylation and N-acylation of amines

Amirsoleimani, Mina,Khalilzadeh, Mohammad A.,Zareyee, Daryoush

, (2020/08/22)

Novel palladium nanoparticles stabilized by clinoptilolite as a natural inexpensive zeolite prepared and used for N-formylation and N-acylation of amines at room temperature at environmentally benign reaction conditions in good to excellent yields. Pd (II) was immobilized on the surface of clinoptilolite via facile multi-step amine functionalization to obtain a sustainable, recoverable, and highly active nano-catalyst. The structural and morphological characterizations of the catalyst carried out using XRD, FT-IR, BET and TEM techniques. Moreover, the catalyst is easily recovered using simple filtration and reused for 7 consecutive runs without any loss in activity.

Process route upstream and downstream products

Process route

4-nitrophenol acetate
830-03-5

4-nitrophenol acetate

aniline
62-53-3

aniline

Acetanilid
103-84-4

Acetanilid

Conditions
Conditions Yield
In water; at 30 ℃; Rate constant; also DMSO as a solvent;
O-(4-methoxybenzoyl)-N-phenyl-acetohydroxamic acid
1309926-78-0

O-(4-methoxybenzoyl)-N-phenyl-acetohydroxamic acid

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Acetanilid
103-84-4

Acetanilid

Conditions
Conditions Yield
With water; In methanol; for 0.833333h; UV-irradiation;
Diphenylmethane
101-81-5

Diphenylmethane

acetyl chloride
75-36-5

acetyl chloride

benzonitrile
100-47-0

benzonitrile

Acetanilid
103-84-4

Acetanilid

Conditions
Conditions Yield
Diphenylmethane; With sodium azide; oxygen; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; at 40 ℃; for 4h; Sealed tube;
acetyl chloride;
80%
70%
ethyl 3-oxo-3-phenylpropionate
94-02-0

ethyl 3-oxo-3-phenylpropionate

benzonitrile
100-47-0

benzonitrile

Acetanilid
103-84-4

Acetanilid

Conditions
Conditions Yield
With hydroxylamine hydrochloride; trifluoroacetic acid; at 70 ℃; for 16h; Inert atmosphere;
Conditions
Conditions Yield
at 906 ℃; Product distribution; pyrolyses, tubular reactor; different feeding conditions, other temperatures between 750 and 950 deg C;
9%
7%
6%
5%
2%
2%
acetic acid
64-19-7,77671-22-8

acetic acid

nitrobenzene
98-95-3,26969-40-4

nitrobenzene

N-acetyl-N-phenylacetamide
1563-87-7

N-acetyl-N-phenylacetamide

aniline
62-53-3

aniline

Acetanilid
103-84-4

Acetanilid

Conditions
Conditions Yield
With hydrogen; at 80 ℃; for 24h; under 760.051 Torr; Sealed tube;
thioacetanilide
637-53-6

thioacetanilide

copper diacetate
142-71-2

copper diacetate

N-acetyl-N-phenylacetamide
1563-87-7

N-acetyl-N-phenylacetamide

Acetanilid
103-84-4

Acetanilid

Conditions
Conditions Yield
In dichloromethane; for 720h; Product distribution; Ambient temperature;
acetic anhydride
108-24-7

acetic anhydride

aniline
62-53-3

aniline

N-acetyl-N-phenylacetamide
1563-87-7

N-acetyl-N-phenylacetamide

Acetanilid
103-84-4

Acetanilid

Conditions
Conditions Yield
Product distribution; 1 stdg. Kochen;
(E)-ethanone-1-phenyl-O-(phenylmethyl)oxime
28570-76-5,106770-94-9

(E)-ethanone-1-phenyl-O-(phenylmethyl)oxime

benzaldehyde
100-52-7

benzaldehyde

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

Acetanilid
103-84-4

Acetanilid

acetonitrile
75-05-8,26809-02-9

acetonitrile

Conditions
Conditions Yield
at 250 ℃; for 24h; Product distribution; Mechanism;
12.5%
13%
14%
10.5%
11.5%
3.75%
acetoxy-(<i>N</i>-acetyl-anilino)-phenyl-methane
55023-62-6

acetoxy-(N-acetyl-anilino)-phenyl-methane

benzaldehyde
100-52-7

benzaldehyde

Acetanilid
103-84-4

Acetanilid

Conditions
Conditions Yield

Global suppliers and manufacturers

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  • Hangzhou Dingyan Chem Co., Ltd
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  • Simagchem Corporation
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  • Amadis Chemical Co., Ltd.
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  • Chemwill Asia Co., Ltd.
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