95-66-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-m-xylene is used as a reagent in the synthesis of 5-aryloxy-2,4-thiazolidinediones, which are potent GPR40 agonists. GPR40 is a G-protein coupled receptor that plays a crucial role in glucose homeostasis and insulin secretion. Agonists of GPR40 have been found to improve insulin sensitivity and lower blood glucose levels, making them potential therapeutic agents for the treatment of type 2 diabetes.
In the synthesis process, 4-chloro-m-xylene serves as a key intermediate, providing the necessary structural elements for the formation of the final product. The chlorine atom in the molecule can be replaced by other functional groups, such as hydroxyl or amino groups, through various chemical reactions, allowing for the creation of a wide range of 5-aryloxy-2,4-thiazolidinedione derivatives with different biological activities and properties.
Furthermore, 4-chloro-m-xylene can also be used as a building block in the synthesis of other pharmaceutical compounds, agrochemicals, and specialty chemicals, owing to its reactive chlorine atom and the presence of the benzene ring with methyl substituents. Its versatility and reactivity make it an important chemical intermediate in various chemical and pharmaceutical processes.

InChI:InChI=1/C8H9Cl/c1-6-3-4-8(9)7(2)5-6/h3-5H,1-2H3

Upstream product

• 88-61-9 2,4-dimethylbenzenesulfonic acid 
• 34896-68-9 2-chloro-5-methylbenzyl chloride 
• 27876-29-5 acetic acid-(2,4,6,N-tetrachloro-anilide) 
• 64-19-7 acetic acid 
• 108-38-3 m-xylene 
• 95-68-1 2,4-Xylidine 
• 35709-99-0 chlorocarbonic acid-(2,4-dimethyl-phenyl ester) 
• 7791-25-5 sulfuryl dichloride 
• 7553-56-2 iodine 
• 7782-50-5 chlorine 
• 7705-08-0 iron(III) chloride 
• 7446-70-0 aluminium trichloride 
• 106-43-4 para-chlorotoluene 
• 95-47-6 o-xylene 

Downstream Products

• 17961-80-7 (2,4-dimethylphenyl)(trimethyl)silan 
• 7697-29-2 4-chloro-3-methylbenzoic acid 
• 2845-85-4 4-chloroisophthalic acid 
• 27260-64-6 4-chloro-1,3-bis-(trichloromethyl)-benzene 
• 117890-58-1 4-(bromomethyl)-1-chloro-2-methylbenzene 
• 69383-68-2 1-chloro-2,4-dimethyl-5-nitrobenzene 
• 103039-07-2 1-(2-chloro-3,5-dimethyl-phenyl)-ethanone 
• 13520-08-6 1-chloro-2,4-bis-dichloromethyl-benzene 
• 3976-36-1 2,2',4,4'-tetramethylbiphenyl 
• 108-38-3 m-xylene 
• 76154-76-2 N,N'-bis(2,4-dimethylphenyl)-p-phenylenediamine 
• 60047-41-8 4-chloro-isophthalic acid dimethyl ester 
• 21900-24-3 3-methyl-4-chloro benzoylchloride 
• 101349-71-7 4-Chloro-3-methylbenzaldehyde 

Relevant academic research and scientific papers

Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes

A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photo-oxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates.

A 3,5-dimethyl aniline method for the preparation of

The invention discloses a preparation method of 3, 5-dimethylaniline. The preparation method is used for preparing the target product 3, 5-dimethylaniline through a reaction of chlorination, nitration and catalytic reductive dechlorination of a ring by taking m-xylene as a raw material. Compared with existing processes, the method disclosed by the invention is few in reaction step and simple in technological process. The yield of 3, 5-dimethylaniline based on m-xylene can reach over 75% of a theoretical amount. The cost of the 3, 5-dimethylaniline can be greatly lowered.

Aromatic substitution in ball mills: Formation of aryl chlorides and bromides using potassium peroxomonosulfate and NaX

Aryl chlorides and bromides are formed from arenes in a ball mill using KHSO5 and NaX (X = Cl, Br) as oxidant and halogen source, respectively. Investigation of the reaction parameters identified operating frequency, milling time, and the number of milling balls as the main influencing variables, as these determine the amount of energy provided to the reaction system. Assessment of liquid-assisted grinding conditions revealed, that the addition of solvents has no advantageous effect in this special case. Preferably activated arenes are halogenated, whereby bromination afforded higher product yields than chlorination. Most often reactions are regio- and chemoselective, since p-substitution was preferred and concurring side-chain oxidation of alkylated arenes by KHSO5 was not observed. The Royal Society of Chemistry.

Gold-catalyzed halogenation of aromatics by N-halosuccinimides

(Chemical Equation Presented) Golden bromination: A highly efficient and mild AuCl3-catalyzed bromination of aromatic rings with Nbromosuccinimide (NBS) has been developed. This method works with a low catalyst loading (down to 0.01 mol %) and can be combined with transition metal catalyzed transformations to deliver various aryl products.

Regiospecific chlorination of xylenes using K-10 montmorrillonite clay

Regiospecific chlorination of xylenes has been developed by employing NCS as a reagent and K-10 montmorrillonite clay as a solid support. Copyright Taylor & Francis Group, LLC.

Grindstone chemistry: (Diacetoxyiodo)benzene-mediated oxidative nuclear halogenation of arenes using NaCl, NaBr or I2

A technique of "Grindstone chemistry" is applied to the solvent-free halogenation of arenes with NaCl, NaBr or I2 using (diacetoxyiodo)benzene as the oxidant. Improved yields and higher purities of the products are observed compared with those from established methods.

PROCESS FOR HALOGENATION OF BENZENE AND BENZENE DERIVATIVES

In a process of halogenation of benzene or benzene derivatives, di-substituted halobenzene derivatives having para-aromatic compounds or tri-substituted halobenzene derivatives having 1,2,4-substituted aromatic compounds are selectively produced. In halogenation of benzene or benzene derivatives, a fluorine-containing zeolite catalyst such as L-type zeolite, or a zeolite catalyst having the crystal size of at most 100 nm is used. The reaction is preferably effected in the presence of a solvent, and the solvent is preferably a halogenated compound.

A simple, efficient and regioselective oxychlorination of aromatic compounds using ammonium chloride and oxone

A simple, efficient, mild and regioselective method for oxychlorination of aromatic compounds is reported. The electrophilic substitution of chlorine generated in situ from NH4Cl as a chlorine source and oxone as an oxidant is reported for the first time.

Oxidative halogenation of aromatic compounds with metal halides and sodium bismuthate

A new mild and efficient method for aromatic halogenation with a wide variety of halides in the presence of sodium bismuthate NaBO3 in AcOH is reported. Metal halides of groups Ia, IIa, IIIa, IVa, Va, and the first row of transition elements are suitable for this method.

Chlorination of aromatic compounds with chlorous acid under non-aqueous conditions

The non-aqueous solution of chlorous acid is a versatile chlorinating agent for aromatic compounds, e.g. alkylbenzenes, anisoles, and acetanililides. It is also an effective chlorine-substitute for the conversion of aryl bromides into aryl chlorides under mild conditions. The stoichiometry of the chlorination reaction is ArH+3HOClO→ArCl+2ClO2+2H2O, and the mode of dissociation of chlorous acid in dichloromethanc is 3HOClO→HOCl+2ClO2+H2O.