7149-79-3

Usage

Uses

Used in Chemistry Research Industry:
3-Chloro-4-methylacetanilide is used as a reagent for various chemical reactions and processes, facilitating the synthesis of more complex compounds. Its unique structure and properties make it a valuable building block in the development of new chemical entities.
3-Chloro-4-methylacetanilide is also used as a reference standard in analytical chemistry, allowing researchers to compare and quantify the purity and composition of other compounds.
Furthermore, it serves as a precursor in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals, contributing to the advancement of these industries.

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

Upstream product

• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 95-74-9 3-chloro-p-toluidine 
• 75-36-5 acetyl chloride 
• 7647-01-0 hydrogenchloride 
• 121-86-8 2-chloro-4-nitrotoluene 
• 10387-40-3 potassium thioacetate 
• 95-49-8 2-methylchlorobenzene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 1338235-62-3 C₉H₇Cl 
• 103-89-9 4-Methylacetanilide 
• 75-05-8 acetonitrile 
• 98-09-9 benzenesulfonyl chloride 
• 71-55-6 1,1,1-trichloroethane 

Downstream Products

• 7149-78-2 5-chloro-4-methyl-2-nitroacetanilide 
• 38667-55-9 4-Acetylamino-2-chlorobenzoic acid 
• 7149-80-6 5-chloro-4-methyl-2-nitroaniline 
• 136403-10-6 acetic acid-(2,3-dichloro-4-methyl-anilide) 
• 116010-06-1 N-(2-bromo-5-chloro-4-methylphenyl)acetamide 
• 439096-91-0 acetic acid-(3-chloro-4-methyl-2,6-dinitro-anilide) 
• 861611-40-7 acetic acid-(5-chloro-2-chloroacetyl-4-methyl-anilide) 
• 1204312-39-9 4-chloro-5-methyl-N-acetylanthranilic acid 
• 42832-87-1 3,6-diaminoacridin-9(10H)-one 
• 857612-73-8 1,6-diamino-10H-acridin-9-one 

Relevant academic research and scientific papers

Direct Superacid-Promoted Difluoroethylation of Aromatics

Under superacid conditions, aromatic amines are directly and regioselectively 1,1-difluoroethylated. Low temperature in situ NMR studies confirmed the presence of benzylic α-fluoronium and α-chloronium ions as key intermediates in the reaction. This method has a wide substrate scope and can be applied to the late-stage functionalization of natural alkaloids and active pharmaceutical ingredients.

Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.

Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation

Under superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation of arenes is complementary to existing methods and can be applied, through protection by protonation, to the late-stage site-selective functionalization of natural alkaloids and active pharmaceutical ingredients.

Complementary Site-Selective Halogenation of Nitrogen-Containing (Hetero)Aromatics with Superacids

Site-selective functionalization of arenes that is complementary to classical aromatic substitution reactions remains a long-standing quest in organic synthesis. Exploiting the generation of halenium ion through oxidative process and the protonation of the nitrogen containing function in HF/SbF5, the chlorination and iodination of classically inert Csp2?H bonds of aromatic amines occurs. Furthermore, the superacid-promoted (poly)protonation of the molecules acts as a protection, favoring the late-stage selective halogenation of natural alkaloids and active pharmaceutical ingredients.

Proliferation inhibition of novel diphenylamine derivatives

Nonsteroidal anti-inflammatory drugs (NSAIDs) are the most widely used drugs in the world but some NSAIDs such as diclofenac and tolfenamic acid display levels of cytotoxicity, an effect which has been attributed to the presence of diphenylamine contained in their structures. A novel series of diphenylamine derivatives were synthetised and evaluated for their cytotoxic activities and proliferation inhibition. The most active compounds in the cytotoxicity tests were derivative 6g with an IC50 value of 2.5 ± 1.1 × 10?6 M and derivative 6f with an IC50 value of 6.0 ± 3.0 × 10?6 M (L1210 cell line) after 48 h incubation. The results demonstrate that leukemic L1210 cells were much more sensitive to compounds 6f and 6g than the HEK293T cells (IC50 = 35 × 10?6 M for 6f and IC50 > 50 × 10?6 M for 6g) and NIH-3T3 (IC50 > 50 × 10?6 M for both derivatives). The IC50 values show that these substances may selectively kill leukemic cells over non-cancer cells. Cell cycle analysis revealed that a primary trend of the diphenylamine derivatives was to arrest the cells in the G1-phase of the cell cycle within the first 24 h. UV–visible, fluorescence spectroscopy and circular dichroism were used in order to study the binding mode of the novel compounds with DNA. The binding constants determined by UV–visible spectroscopy were found to be in the range of 2.1–8.7 × 104 M?1. We suggest that the observed trend for binding constant K is likely to be a result of different binding thermodynamics accompanying the formation of the complexes.

Method for preparing prucalopride

The invention provides a method for preparing prucalopride. The method comprises the following steps: taking 3-chloro-4-methylaniline as an initial raw material, performing amino protection, nucleophilic substitution, hydroxy protection, aromatic hydrocarbon chlorination, free radical bromination, hydrolysis, molecular Friedel-Crafts alkylation reaction ring closure, amino deprotection and oxidative amidation, thereby obtaining the prucalopride. According to the scheme, a dangerous process is not adopted, any highly toxic reagent is not used, the method is safe, green and environmental-friendly, the amount of by-products produced in the reaction is small, and the yield is improved.

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

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.

Efficient Heterogeneous Gold(I)-Catalyzed Direct C(sp2)–C(sp) Bond Functionalization of Arylalkynes through a Nitrogenation Process to Amides

The first heterogeneous gold(I)-catalyzed direct C(sp2)–C(sp) bond functionalization of arylalkynes through a nitrogenation process to amides has been achieved by using an ordered mesoporous silica (MCM-41)-immobilized phosphine gold(I) complex [MCM-41-PPh3-AuCl] as catalyst and silver carbonate (Ag2CO3) as cocatalyst with trimethylsilyl azide (TMSN3) as a nitrogen source, yielding a variety of amides in moderate to excellent yields under mild conditions. This heterogeneous phosphine gold(I) complex shows the same turnover numbers as the homogeneous chloro(triphenylphosphine)gold(I) (Ph3PAuCl) and can easily be recovered by simple filtration of the reaction solution and recycled at least eight times without significant loss of activity, providing a novel, efficient, practical and economic method for the synthesis of amides from alkynes. (Figure presented.).

BENZAMIDE DERIVATIVE

The present invention relates to benzamide derivatives represented by formula (I) or pharmaceutically acceptable salts thereof.

QUINAZOLINEDIONE DERIVATIVE

The present invention relates to quinazolinedione derivatives represented by formula (I) or pharmaceutically acceptable salts thereof.