16634-82-5

Basic information

• Product Name: 2-CHLORO-N-(4-METHYLPHENYL)ACETAMIDE
• Synonyms: ACETAMIDE, 2-CHLORO-N-(4-METHYLPHENYL)-;AKOS B015627;AKOS BC-3032;AKOS BBS-00003959;ART-CHEM-BB B015627;CHEMBRDG-BB 3015627;N-CHLOROACETYL-P-TOLUIDINE;N-(Chloroacetyl)-4-methylaniline
• CAS NO: 16634-82-5
• Molecular Formula: C₉H₁₀ClNO
• Molecular Weight: 183.63
• Product Categories: Anilines, Amides & Amines;Chlorine Compounds;Aromatic Building Blocks
• Mol File: 16634-82-5.mol
• Article Data: 119

Chemical Properties

• Melting Point: 164-166
• Boiling Point: 91°C (rough estimate)
• Flash Point: 160.8 °C
• Appearance: /
• Density: 1.1611 (rough estimate)
• Vapor Pressure: 0.000153mmHg at 25°C
• Refractive Index: 1.5330 (estimate)
• PKA: 12.90±0.70(Predicted)
• CAS DataBase Reference: 2-CHLORO-N-(4-METHYLPHENYL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-(4-METHYLPHENYL)ACETAMIDE(16634-82-5)
• EPA Substance Registry System: 2-CHLORO-N-(4-METHYLPHENYL)ACETAMIDE(16634-82-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 16634-82-5(Hazardous Substances Data)

Usage

General Description

2-Chloro-N-(4-methylphenyl)acetamide is a chemical compound with the molecular formula C9H10ClNO. It is a white solid with a molecular weight of 185.63 g/mol. 2-CHLORO-N-(4-METHYLPHENYL)ACETAMIDE is used in the pharmaceutical industry as an intermediate in the synthesis of various pharmaceuticals and related compounds. It is also used as a building block in the preparation of new chemical entities. Additionally, it has been studied for its potential antibacterial and antifungal properties. 2-Chloro-N-(4-methylphenyl)acetamide is considered to be stable under normal conditions, but should be stored and handled with proper safety precautions in place.

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

Upstream product

• 106-49-0 p-toluidine 
• 79-11-8 chloroacetic acid 
• 120087-93-6 p-toluidine; chloroacetate 
• 67-66-3 chloroform 
• 10026-13-8 phosphorus pentachloride 
• 102878-71-7 2-hydroxy-N-(4-methylphenyl)acetamide 
• 541-88-8 Chloroacetic anhydride 
• 63911-83-1 1,1,1-trimethyl-N-(4-methylphenyl)silanamine 
• 79-04-9 chloroacetyl chloride 
• 5343-65-7 2-bromo-N-p-tolylacetamide 
• 89523-40-0 N¹-Tosyl-N¹,N²-di(p-methylphenyl)-acetamidine 
• 4015-58-1 monochloroacetic acid anhydride 

Downstream Products

• 128890-25-5 2-(2,2-Dimethyl-4-oxo-chroman-7-yloxy)-N-p-tolyl-acetamide 
• 84570-76-3 Triethyl-(p-tolylcarbamoyl-methyl)-ammonium; chloride 
• 89473-82-5 2-Piperazin-1-yl-N-p-tolyl-acetamide 
• 206280-69-5 2-(3-Cyano-6-methyl-4-trifluoromethyl-pyridin-2-ylsulfanyl)-N-p-tolyl-acetamide 
• 64178-02-5 (3-chloro-2-chloromethyl-6-methyl-quinolin-4-yl)-p-tolyl-amine 
• 858004-30-5 4-(2-chloro-acetylamino)-toluene-2-sulfonyl chloride 
• 64642-18-8 2-amino-N-(p-tolyl)acetamide 
• 867350-36-5 2-(4-cyano-5,6-dimethyl-pyridazin-3-ylsulfanyl)-N-p-tolyl-acetamide 
• 912363-09-8 2-(3-phenyl-quinoxalin-2-ylsulfanyl)-N-p-tolyl-acetamide 
• 1055326-02-7 2-{5-[4-(4,6-dimorpholin-4-yl-[1,3,5]triazin-2-ylamino)phenyl](4-methyl-4H-[1,2,4]triazol-3-yl)sulfanyl}-N-p-tolylacetamide 
• 445421-73-8 2-[6-(4,6-dimorpholin-4-yl-[1,3,5]triazin-2-ylamino)benzothiazol-2-ylsulfanyl]-N-p-tolylacetamide 
• 1134193-66-0 6-methyl-4-p-tolyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one 
• 1134193-40-0 3,4-dihydro-4-(4-methylphenyl)-3-oxo-2H-1,4-benzoxazine 

Relevant articles and documents

An Expedient Process for the Synthesis of 2-(N -Arylamino)benzaldehydes from 2-Hydroxybenzaldehydes via Smiles Rearrangement

This paper describes an efficient Smiles rearrangement process for the synthesis of 2-(N-arylamino)benzaldehyde derivatives with reasonable yields. A mechanism is proposed for the reaction course. Georg Thieme Verlag Stuttgart, New York.

Design, synthesis, docking study, α-glucosidase inhibition, and cytotoxic activities of acridine linked to thioacetamides as novel agents in treatment of type 2 diabetes

A novel series of acridine linked to thioacetamides 9a–o were synthesized and evaluated for their α-glucosidase inhibitory and cytotoxic activities. All the synthesized compounds exhibited excellent α-glucosidase inhibitory activity in the range of IC50 = 80.0 ± 2.0–383.1 ± 2.0 μM against yeast α-glucosidase, when compared to the standard drug acarbose (IC50 = 750.0 ± 1.5 μM). Among the synthesized compounds, 2-((6-chloro-2-methoxyacridin-9-yl)thio)-N-(p-tolyl) acetamide 9b displayed the highest α-glucosidase inhibitory activity (IC50 = 80.0 ± 2.0 μM). The in vitro cytotoxic assay of compounds 9a–o against MCF-7 cell line revealed that only the compounds 9d, 9c, and 9n exhibited cytotoxic activity. Cytotoxic compounds 9d, 9c, and 9n did not show cytotoxic activity against the normal human cell lines HDF. Kinetic study revealed that the most potent compound 9b is a competitive inhibitor with a Ki of 85 μM. Furthermore, the interaction modes of the most potent compounds 9b and 9f with α-glucosidase were evaluated through the molecular docking studies.

Synthesis and luminescence properties of 1,3,4-oxadiazole acetamide derivatives and their rare earth complexes

A series of 1,3,4-oxadiazole acetamide derivatives have been designed and synthesized, and their complexes with Eu(III) and Tb(III) were also prepared. The luminescence properties of the target complexes were investigated, and the results indicated that a

Optimization of pyrrolizine-based Schiff bases with 4-thiazolidinone motif: Design, synthesis and investigation of cytotoxicity and anti-inflammatory potency

Two new series of pyrrolizine-5-carboxamides were synthesized and evaluated for their anticancer and anti-inflammatory activities. The new compounds exhibited potent cytotoxicity (IC50 = 0.10–22.96 μM) against three cancer (MCF-7, A2780 and HT2

Synthesis, characterization and properties of salicylhydrazide-salicylacylhydrazone derivatives and their terbium complexes

A series of terbium complexes with salicylhydrazide-salicylacylhydrazone derivatives were synthesized and characterized by elemental analysis, IR spectra, UV/vis spectra and thermal analysis. The luminescence and electrochemical properties of the terbium complexes were investigated. The results show that all the target complexes exhibited characteristic emissions of terbium ions and the complex substituted by the chlorine has the strongest luminescence intensity with the highest quantum yield at 0.609. The introduction of donating electron groups could increase the oxidation potential and the highest occupied molecular orbital energy level of the terbium complex; however, the introduction of accepting electron groups gave the opposite result.

Novel pyrrolizines bearing 3,4,5-trimethoxyphenyl moiety: design, synthesis, molecular docking, and biological evaluation as potential multi-target cytotoxic agents

In the present study, two new series of pyrrolizines bearing 3,4,5-trimethoxyphenyl moiety were designed, synthesised, and evaluated for their cytotoxic activity. The benzamide derivatives 16a–e showed higher cytotoxicity than their corresponding Schiff b

Inhibition of Autophagy by a Small Molecule through Covalent Modification of the LC3 Protein

The autophagic ubiquitin-like protein LC3 functions through interactions with LC3-interaction regions (LIRs) of other autophagy proteins, including autophagy receptors, which stands out as a promising protein–protein interaction (PPI) target for the intervention of autophagy. Post-translational modifications like acetylation of Lys49 on the LIR-interacting surface could disrupt the interaction, offering an opportunity to design covalent small molecules interfering with the interface. Through screening covalent compounds, we discovered a small molecule modulator of LC3A/B that covalently modifies LC3A/B protein at Lys49. Activity-based protein profiling (ABPP) based evaluations reveal that a derivative molecule DC-LC3in-D5 exhibits a potent covalent reactivity and selectivity to LC3A/B in HeLa cells. DC-LC3in-D5 compromises LC3B lipidation in vitro and in HeLa cells, leading to deficiency in the formation of autophagic structures and autophagic substrate degradation. DC-LC3in-D5 could serve as a powerful tool for autophagy research as well as for therapeutic interventions.

Antidiabetic compounds

Compounds for the treatment of hyperglycemia and/or diabetes are provided. The compounds, which inhibit the enzyme dipeptidyl peptidase (DPP-4), are based on the structure where X may be present or absent an may be OH, Ar is an aryl group; and n ranges from 0 to 5.