95-66-9

Basic information

• Product Name: 4-CHLORO-M-XYLENE
• Synonyms: 4-CHLORO-M-XYLENE;1-CHLORO-2,4-DIMETHYLBENZENE;m-Xylene, 4-chloro-;4-Chloro-m-xylene,97%;4-CHLORO-M-XYLENE 98%;S26-37;2,4-Dimethyl-1-chlorobenzene;4-Chloro-1,3-dimethylbenzene
• CAS NO: 95-66-9
• Molecular Formula: C₈H₉Cl
• Molecular Weight: 140.61
• Product Categories: Halogen toluene;Chlorine Compounds
• Mol File: 95-66-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: -32 °C
• Boiling Point: 187 °C
• Flash Point: 62.1 °C
• Appearance: /
• Density: 1.06
• Vapor Pressure: 0.866mmHg at 25°C
• Refractive Index: 1.5220-1.5260
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-CHLORO-M-XYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-M-XYLENE(95-66-9)
• EPA Substance Registry System: 4-CHLORO-M-XYLENE(95-66-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36
• Hazardous Substances Data: 95-66-9(Hazardous Substances Data)

Usage

Description

4-Chloro-m-xylene, also known as 1-chloro-3-xylene, is an organic compound with the chemical formula C8H9Cl. It is a colorless liquid with a characteristic aromatic odor. The molecule consists of a benzene ring with two methyl groups (-CH3) in the meta position (1,3-positions) and a chlorine atom (-Cl) attached to the 4th carbon atom. This chemical structure makes it a versatile intermediate in the synthesis of various organic compounds.

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 articles and documents

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.

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.

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.