7463-35-6

Basic information

• Product Name: 3-CHLORO-2-METHYLACETANILIDE
• Synonyms: 3'-CHLORO-O-ACETOTOLUIDIDE;3-CHLORO-2-METHYL-N-ACETYLANILINE;3'-CHLORO-2'-METHYLACETANILIDE;3-CHLORO-2-METHYLACETANILIDE;N-(3-chloro-2-methylphenyl)acetamide;3'-Chloro-2'-methylacetanilide,98%;N-(2-Methyl-3-chlorophenyl)acetamide;N-(3-chloro-2-methyl-phenyl)ethanamide
• CAS NO: 7463-35-6
• Molecular Formula: C₉H₁₀ClNO
• Molecular Weight: 183.63
• EINECS: 231-254-2
• Product Categories: Anilines, Amides & Amines;Chlorine Compounds
• Mol File: 7463-35-6.mol

Chemical Properties

• Melting Point: 155-157°C
• Boiling Point: 317.2 °C at 760 mmHg
• Flash Point: 145.7 °C
• Appearance: /
• Density: 1.218 g/cm³
• Vapor Pressure: 0.00039mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: 3-CHLORO-2-METHYLACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-2-METHYLACETANILIDE(7463-35-6)
• EPA Substance Registry System: 3-CHLORO-2-METHYLACETANILIDE(7463-35-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 7463-35-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-2-methylacetanilide is used as an intermediate in the manufacturing of pharmaceuticals for its analgesic and antipyretic properties. It aids in the development of medications aimed at pain relief and fever reduction.
Used in Dye Industry:
3-Chloro-2-methylacetanilide is used as an intermediate in the production of dyes, contributing to the creation of various colorants for different applications.
Used in Pesticide Industry:
3-Chloro-2-methylacetanilide is used as an intermediate in the manufacturing of pesticides, leveraging its potential to control and manage pests in agricultural settings.
Used in Antimicrobial Development:
3-Chloro-2-methylacetanilide is used as a potential candidate for the development of new antimicrobial agents due to its demonstrated antibacterial and antifungal activity. This application is crucial in the ongoing battle against antibiotic-resistant bacteria and the need for novel antifungal treatments.

InChI:InChI=1/C9H10ClNO/c1-6-8(10)4-3-5-9(6)11-7(2)12/h3-5H,1-2H3,(H,11,12)

Upstream product

• 6259-40-1 3-chloro-2-methyl-aniline; hydrochloride 
• 108-24-7 acetic anhydride 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 88-72-2 1-methyl-2-nitrobenzene 
• 64-19-7 acetic acid 
• 127-19-5 N,N-dimethyl acetamide 
• 83-42-1 6-chloro-2-nitrotoluene 

Downstream Products

• 51123-58-1 acetic acid-(3-chloro-2-methyl-6-nitro-anilide) 
• 19407-42-2 2-(acetylamino)-6-chlorobenzoic acid 
• 131923-69-8 2,7-dichloro- 8-methyl-3-formylquinoline 
• 13096-96-3 4-chloro-1H-indazole 
• 145439-15-2 N-acetyl-4-chloro-1H-indazole 
• 72290-22-3 3-Acetylsulfamoyl-2-chloro-6-ethylamino-benzoic acid 
• 72290-18-7 6-acetylamino-2-chloro-3-sulfamoyl-benzoic acid 
• 1954-94-5 4-amino-2-chlorobenzenesulfonamide 
• 21147-93-3 1,6-Dichlor-fluorenon 
• 50-30-6 2,6-dichlorobenzoic acid 
• 131885-51-3 4-Chloro-5-imidazol-1-yl-3-methyl-2-nitro-phenylamine 
• 131885-48-8 3-Imidazol-1-yl-2-methyl-6-nitro-phenylamine 
• 131886-00-5 4-Chloro-5-imidazol-1-yl-3-methyl-benzene-1,2-diamine 
• 131885-38-6 3-amino-5,6-dichloro-2-nitrotoluene 

Relevant articles and documents

Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water

Developing and/or modifying fundamental chemical reactions using chemical industry-favorite heterogeneous recoverable catalytic systems in the water solvent is very important. In this paper, we developed convenient, green, and efficient approaches for the chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes in the presence of the recoverable heterogeneous carbon-supported palladium (Pd/C) catalytic system in water. The utilize of the simple, effective, and recoverable catalyst and also using of water as an entirely green solvent along with relatively short reaction times and good-to-excellent yields of the desired products are some of the noticeable features of the presented synthetic protocols. Graphic abstract: [Figure not available: see fulltext.].

Synthetic method 5- of -4- (-1- I -3-)-(C)-(C)-ethyl-methyl-indol. (by machine translation)

To the method, the 3 - indole chromogenic 5 - substrate is obtained, by hydrolyzing the indole phenol with acetic. anhydride, under an acidic condition with acetic, anhydride to form an indole, chromogenic substrate by hydrolyzing the, indole phenol, with acetic anhydride under an acidic, condition with acetic anhydride under an acidic condition 5 - 5 . (by machine translation)

Anti-malarial, cytotoxicity and molecular docking studies of quinolinyl chalcones as potential anti-malarial agent

Abstract: The quinolinyl chalcones series (A1–A14) were screened for antimalarial activity. According to in vitro antimalarial studies, many quinolinyl chalcones are potentially active against CQ-sensitive and resistance P. falciparum strains with no toxicity against Vero cell lines. The most active quinolinyl chalcones A4 (with IC50 0.031?μM) made a stable A4–heme complex with ??25?kcal/mole binding energy and also showed strong π–π interaction at 3.5??. Thus, the stable A4–heme complex formation suggested that these quinolinyl chalcones act as a blocker for heme polymerization. The docking results of quinolinyl chalcones with Pf-DHFR showed that the halogenated benzene part of quinolinyl chalcones made strong interaction with Pf-DHFR as compared to quinoline part. A strong A4–Pf-DHFR complex was formed with low binding energy (??11.04?kcal/mole). The ADMET properties of quinolinyl chalcones were also studied. The in vivo antimalarial studies also confirmed the A4 as an active antimalarial agent. Graphical abstract: [Figure not available: see fulltext.].

Ni2B@Cu2O and Ni2B@CuCl2: two new simple and efficient nanocatalysts for?the green one-pot reductive acetylation of nitroarenes and direct N-acetylation of arylamines using solvent-free mechanochemical grinding

Abstract: Ni2B@Cu2O and Ni2B@CuCl2 are introduced as simple and efficient earth-abundant transition-metal-based nanocomposites for the?green one-pot reductive acetylation of aromatic nitro compounds and direct N-acetylation of arylamines using a solvent-free mechanochemical grinding technique. The designed Ni2B-based nanocomposites were characterized by Fourier-transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD) analysis, and scanning electron microscopy (SEM) with energy-dispersive X-ray (EDX) spectroscopy. Notable advantages of these methods include broad substrate scope, use of a solvent-free mechanochemical grinding technique, implementation of earth-abundant transition-metal-based nanocomposites as simple and practical catalysts, and short reaction time and high yield at ambient condition. The mentioned methods can also be successfully applied for the?synthesis of a broad range of other amides (especially substituted acetamides) using green chemistry protocols. Also, the recoverability and reusability of the mentioned new nanocomposites were investigated. Graphical abstract: [Figure not available: see fulltext.].

Copper-(II) Catalyzed N-Formylation and N-Acylation of Aromatic, Aliphatic, and Heterocyclic Amines and a Preventive Study in the C-N Cross Coupling of Amines with Aryl Halides

A Cu-(II) catalyzed N-formylation and N-acylation of amines with moderate to excellent yields, using N, N-dimethyl formamide (DMF) and N, N-dimethyl acetamide (DMA) as a formyl and acylating sources in the presence of 1,2,4-triazole is reported. This novel, highly efficient and simple protocol shows broad substrate scope for aliphatic, aromatic, and heterocyclic amines. In addition, the conditions to prevent N-formylation and N-acylation impurities in the C?N cross coupling of amines and aryl halides are described typically when DMF and DMA are used as solvents, with various catalysts, ligands, and bases.

Sulfated choline ionic liquid-catalyzed acetamide synthesis by grindstone method

Sulfated choline ionic liquid (SCIL) has been found to be an efficient solid acid IL catalyst for the protection of amine groups with acetic anhydride under solvent-free grindstone conditions. The attractive features of this new catalytic methodology include its sustainability, facile work-up procedure, economic viability, and biodegradability. The SCIL catalyst was characterized using infrared spectroscopy, wide-angle X-ray scattering analysis, and scanning electron microscopy with energy dispersive X-ray spectroscopy. The catalyst could be reused six times without significant loss in activity. Furthermore, no chromatographic separations were needed to obtain the desired products.

Co3O4 nanoparticles prepared by oxidative precipitation method: an efficient and reusable heterogeneous catalyst for N-formylation of amines

Abstract: N-formylation of different amines was carried out with formic acid in the presence of the Co3O4 nanoparticles as an efficient, stable heterogeneous catalyst to give the corresponding formamides under solvent-free conditions. This method has advantages over the reported methods such as high yields, mild conditions, easy work-up and short reaction times. The catalyst was characterized by different techniques such as XRD, SEM and FT-IR spectroscopy. Graphical Abstract: [Figure not available: see fulltext.]

INHIBITORS OF RENAL OUTER MEDULLARY POTASSIUM CHANNEL

Compounds of Formula I and the pharmaceutically acceptable salts thereof are provided as inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

Synthesis and Herbicidal Activity of Triketone-Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is one of the most important targets for herbicide discovery. In the search for new HPPD inhibitors with novel scaffolds, triketone-quinoline hybrids were designed and subsequently optimized on the basis of the structure-activity relationship (SAR) studies. Most of the synthesized compounds displayed potent inhibition of Arabidopsis thaliana HPPD (AtHPPD), and some of them exhibited broad-spectrum and promising herbicidal activity at the rate of 150 g ai/ha by postemergence application. Most promisingly, compound III-l, 3-hydroxy-2-(2-methoxy-7-(methylthio)quinoline-3-carbonyl)cyclohex-2-enone (Ki = 0.009 ～M, AtHPPD), had broader spectrum of weed control than mesotrione. Furthermore, compound III-l was much safer to maize at the rate of 150 g ai/ha than mesotrione, demonstrating its great potential as herbicide for weed control in maize fields. Therefore, triketone-quinoline hybrids may serve as new lead structures for novel herbicide discovery.

Synthesis, characterization, theoretical, anti-bacterial and molecular docking studies of quinoline based chalcones as a DNA gyrase inhibitor

A series of fourteen (A1-A14) new qunioline based chalcones were synthesized by condensing 2,7-dichloro-8-methyl-3-formyl quinoline with acetophenone and acetylthiophenes, and subsequently characterized by IR, NMR and Mass spectroscopy. All the compounds were screened for antibacterial activities and found potentially active antibacterial agents. Bioassay, theoretical and dockings studies with DNA gyrase (the enzyme required for super coiling of DNA of bacteria) results showed that the type and positions of the substituents seemed to be critical for their antibacterial activities. The bromo and chloro substituted chalcone displayed high anti-bacterial activity. The A4 and A6 showed high interaction with DNA gyrase, contributing high free binding energy (ΔG -8.18 and -8.88 kcal).