1585-15-5

Basic information

• Product Name: 4,6-BIS(CHLOROMETHYL)-M-XYLENE
• Synonyms: 1,5-Bis(chloromethyl)-2,4-dimethylbenzene;1,5-DI(CHLOROMETHYL)-2,4-DIMETHYLBENZENE;4,6-BIS(CHLOROMETHYL)-M-XYLENE;alpha(1),alpha(3)-Dichlorodurene;4,6-BIS(CHLOROMETHYL)-M-XYLENE 95%
• CAS NO: 1585-15-5
• Molecular Formula: C₁₀H₁₂Cl₂
• Molecular Weight: 203.11
• Mol File: 1585-15-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 97 °C
• Boiling Point: 291.9°Cat760mmHg
• Flash Point: 142.6°C
• Appearance: /
• Density: 1.145g/cm³
• Vapor Pressure: 0.0033mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: 4,6-BIS(CHLOROMETHYL)-M-XYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-BIS(CHLOROMETHYL)-M-XYLENE(1585-15-5)
• EPA Substance Registry System: 4,6-BIS(CHLOROMETHYL)-M-XYLENE(1585-15-5)

Safety Data

• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3261
• Hazardous Substances Data: 1585-15-5(Hazardous Substances Data)

Usage

Uses

Used in Epoxy Resin Production:
4,6-Bis(chloromethyl)-m-xylene is used as a crosslinking agent for the production of epoxy resins. It enhances the mechanical properties and chemical resistance of the resins, making them suitable for various applications.
Used in Industrial Coating and Adhesive Manufacturing:
In the manufacturing of industrial coatings and adhesives, 4,6-bis(chloromethyl)-m-xylene serves as a curing agent. Its inclusion improves the adhesion, durability, and performance of the final products, catering to the demands of different industries.
Used in Chemical Synthesis:
4,6-Bis(chloromethyl)-m-xylene is utilized as a chemical intermediate in the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of products, contributing to the versatility of chemical manufacturing processes.
Used in Chemical Industry:
4,6-Bis(chloromethyl)-m-xylene is used as a key component in the chemical industry for the development of new materials and products. Its reactivity and functional groups make it a valuable asset in the synthesis of specialty chemicals and intermediates.

InChI:InChI=1/C10H12Cl2/c1-7-3-8(2)10(6-12)4-9(7)5-11/h3-4H,5-6H2,1-2H3

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 108-38-3 m-xylene 
• 50-00-0 formaldehyd 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 110-88-3 1,3,5-Trioxan 
• 95-47-6 o-xylene 

Downstream Products

• 5312-04-9 1.5-Dimethyl-benzol-2.4-dipropionsaeure 
• 19444-28-1 1,3-Bis-(α-hydroxy-isobutyryloxymethyl)-4,6-dimethyl-benzol 
• 104035-83-8 1,5-Dimethyl-2,4-bis-chlormethyl-3,6-dichlor-benzol 
• 408328-49-4 1,5-bis(chloromethyl)-2,4-dimethyl-3-nitrobenzene 
• 95152-12-8 2,6-bis(chloromethyl)-3,5-dimethyl-1,4-dinitrobenzene 
• 122697-60-3 N-(p-Tolylsulfonyl)-1-thia-14-aza<2>metacyclo<2>(1,3)pyrenophan 
• 122697-61-4 N-(p-Tolylsulfonyl)-1-thia-14-aza<2>metacyclo<2>(1,3)-9,10-dihydropyrenophan 
• 122697-57-8 N-(p-Tolylsulfonyl)<2.2>(1,3)(1,3)-1-thia-10-aza<2.2>(4,6)(1,3)cyclophan 
• 120697-86-1 N-(p-Tolylsulfonyl)-1-thia-14-aza<2>metacyclo<2>(1,3)-4,5,9,10-tetrahydropyrenophan 
• 122697-58-9 N-(p-Tolylsulfonyl)<2.2>(1,3)(1,3)-1-thia-10-aza<2.2>(4,6)(1,3)cyclophan-10,10-dioxid 
• 58074-29-6 1,5-bis(mercaptomethyl)-2,4-dimethylbenzene 
• 140410-15-7 5,7,14,16-Tetrakis(acetoxymethyl)-2,11-ditosyl-2,11-diaza<3.3>metacyclophan 
• 140410-13-5 5,7,14,16-tetrakis(ethoxycarbonyl)-2,11-bis(4-tolylsulfonyl)-2,11-diaza<3.3>metacyclophane 
• 140410-08-8 4,6-Bis(brommethyl)benzol-1,3-dicarbonsaeure-diethylester 

Relevant articles and documents

Synthesis of 5- tert-butyl-8, 12, 14-trimethyl- and 5- tertbutyl- 8, 12, 14, 16-tetramethyI[2.2]metacyclophane and their treatment with lewis acids in benzene

Treatment of 5-tert-butyl-8,12,14,16-tetramethyl[2.2]MCP with AICI 3-MeN02 in benzene led to trans-tert-butylation to afford 8,12,14,16-tetramethyl[2.2]MCP in good yield along with tert-butylbenzene. On the other hand, the same treat

Conformational control of bis-urea self-assembled supramolecular pH switchable low-molecular-weight hydrogelators

We report the synthesis and investigation into the structure-property relationships of eight different low molecular weight hydrogelators based on a bisaromatic urea core unit, all of which form gels as the pH of the solution is lowered. The low molecular weight hydrogelators are functionalized with carboxylic acid moieties on one aromatic ring, and the other aromatic ring features a nitro functional group either in the meta- or paraposition relative to the urea linkage. Ortho-methyl substituents were installed on the aromatic rings to enforce a non-coplanar arrangement between the phenyl and urea moieties. Gel formation was triggered by the addition of a mineral acid or the ring-opening hydrolysis of glucono-δ-lactone. The low molecular weight hydrogelators were studied by a variety of analytical techniques, including NMR spectroscopy and rheology. In addition, their ability to uptake a dye, methylene blue, was determined by UV-vis spectroscopy. (Figure Presented)

Modulation of the coordination geometries of NCN and NCNC Rh complexes for ambidextrous chiral catalysts

A chirality switch between novel NCN pincer Rh complexes and a related double cyclometalated NCNC Rh complex containing secondary amino groups is described. Their catalytic abilities were determined in asymmetric alkynylation of ethyl trifluoropyruvate, a

Synthesis and biological evaluation of dihydropyrano-[2,3-c]pyrazoles as a new class of PPAR? partial agonists

Peroxisome proliferator-activated receptor ? (PPAR?) is a well-known target for thiazolidinedione antidiabetic drugs. In this paper, we present the synthesis and biological evaluation of a series of dihydropyrano[2,3-c]pyrazole derivatives as a novel family of PPAR? partial agonists. Two analogues were found to display high affinity for PPAR? with potencies in the micro molar range. Both of these hits were selective against PPAR?, since no activity was measured when tested against PPARα, PPAR? and RXRα. In addition, a novel modelling approach based on multiple individual flexible alignments was developed for the identification of ligand binding interactions in PPAR?. In combination with cell-based transactivation experiments, the flexible alignment model provides an excellent analytical tool to evaluate and visualize the effect of ligand chemical structure with respect to receptor binding mode and biological activity.

Two birds with one stone: Self-assembly of metal-organic coordination complexes with discrete metallamacrocycle and 1D zigzag chain based on a flexible dicarboxylate ligand

To assemble metal-organic coordination complexes, a flexible dicarboxylate ligand, 2,2′-(4,6-dimethyl-5-nitro-1,3-phenylene)bis(methylene)-bis- (sulfanediyl)dibenzoic acid (H2L), has been designed and synthesized. Using the flexible ligand to a

An experimental and theoretical study on imidazolium-based ionic liquid promoted chloromethylation of aromatic hydrocarbons

The chloromethylation of aromatic hydrocarbons proceeded efficiently using the reusable imidazolium-based ionic liquid as promoter. Mild reaction conditions, enhanced rates, improved yields, recyclability of ionic liquids, and reagents' reactivity which is different from that in conventional organic solvents are the remarkable features observed in ionic liquids. The ionic liquids were recycled in three subsequent runs with no decrease in activity. In addition, the results of calculations with the Gaussian 98 suite of program are in good accordance with the experimental outcomes.

Efficient dichloromethylation of some aromatic hydrocarbons catalyzed by a new ionic liquid [C12minPEG800]br under homogeneous catalysis in aqueous media

A series of new imidazolium-type ionic liquids based on polyethylene glycol have been prepared. The new recyclable temperature-dependant phase-separation system comprised of [C12minPEG800]Br and methylcyclohexane was also developed and successfully applied to the dichloromethylation of some aromatic hydrocarbons to prepare dichloromethyl-substituted hydrocarbons in excellent yields. The ionic liquid could be excellent recycled without any apparent loss of catalytic activity and little loss of weight even after 8 times recycling.

Inclusion of an anion guest within a molecular host formed by (4,6-dimethyl-1,3-phenylene)bis( N , N-dibenzylmethane) and [CuCl 4]2-/[TeCl6]2- through second-sphere coordination

In this work, we have utilized the second-sphere coordination approach toward the construction of supramolecular inclusion solids Cl 2H2O [H2L1]0.5 [CuCl4]0.5 (Crystal 1) and Cl [H2/s

An inexpensive and efficient synthetic method for the preparation of pyromellitic dianhydride promoted by ionic liquid

In this article, pyromellitic dianhydride could be successfully obtained in 76.7% total yield by an aerobic oxidation of 1,4-bis(chloromethyl)-2,5- dimethylbenzene or 1,5-bis(chloromethyl)-2,4- dimethylbenzene catalyzed by VO(acac)2/Cu(2-Eth)2/DABCO in [hmim]OTf and a subsequent dehydration of pyromellitic acid upon heating with acetic anhydride. The starting materials including 1,2-bis(chloromethyl)-4,5-dimethylbenzene were prepared by dichloromethylation of their corresponding xylene catalyzed by [C12mim]Br in aqueous media. ARKAT USA, Inc.

Identification of alkylarene chloromethylation products using gas-chromatographic retention indices

Gas-chromatographic retention indices on standard nonpolar polydimethylsiloxane stationary phases allow identification of products formed by known organic reactions even without using mass-spectrometric data. The efficiency of this approach was demonstrated by the example of identification of previously uncharacterized chloromethyl derivatives of alkylarenes, including structural isomers of compounds containing several chloromethyl groups, directly in reaction mixtures. Chromatographic analysis of such reaction mixtures allows identification of positional isomers of the starting alkylarenes even when they are present simultaneously. The retention indices were determined for the first time for more than 50 alkyl-(chloromethyl)arenes, by-products of chloromethylation, and chloromethyl derivatives of the simplest alkyl phenyl ketones. Nauka/Interperiodica 2007.