824-45-3

Basic information

• Product Name: 2,5-Dimethylbenzyl chloride
• Synonyms: 2-(chloromethyl)-1,4-dimethyl-benzen;2-(Chloromethyl)-1,4-dimethylbenzene;Benzene, 2-(chloromethyl)-1,4-dimethyl-;AKOS BBS-00004039;1-CHLOROMETHYL-2,5-DIMETHYLBENZENE;2,5-DIMETHYLBENZYL CHLORIDE;2-chloromethyl-p-xylene;2,5-Dimethylbenzyl chloride, GC 98%
• CAS NO: 824-45-3
• Molecular Formula: C₉H₁₁Cl
• Molecular Weight: 154.64
• EINECS: 212-529-6
• Product Categories: Aromatic Halides (substituted)
• Mol File: 824-45-3.mol

Chemical Properties

• Melting Point: -43.35°C (estimate)
• Boiling Point: 221-226 °C(lit.)
• Flash Point: 150 °F
• Appearance: clear colorless liquid
• Density: 1.046 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00268mmHg at 25°C
• Refractive Index: n20/D 1.537(lit.)
• Water Solubility: insoluble
• BRN: 2206277
• CAS DataBase Reference: 2,5-Dimethylbenzyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethylbenzyl chloride(824-45-3)
• EPA Substance Registry System: 2,5-Dimethylbenzyl chloride(824-45-3)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 23-26-27-36/37/39-45-25
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 824-45-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 766, 1951 DOI: 10.1021/ja01146a079

InChI:InChI=1/C8H6BrN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2

Upstream product

• 106-42-3 para-xylene 
• 107-30-2 chloromethyl methyl ether 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 95-63-6 1,2,4-Trimethylbenzene 
• 610-72-0 2,5-dimethylbenzoic acid 
• 553-94-6 4-bromo-m-xylene 
• 53957-33-8 2,5-dimethylbenzyl alcohol 
• 7093-91-6 chloromethyl isocyanate 
• 110-88-3 1,3,5-Trioxan 

Downstream Products

• 5779-94-2 2,5-dimethylbenzaldehyde 
• 109936-71-2 N-acetyl-2-ethoxycarbonyl-3-(2,5-dimethylphenyl)-α-alanine ethyl ester 
• 116762-16-4 1-(2,5-dimethylphenyl)-2-butanol 
• 103858-39-5 N-(2,5-dimethylbenzyl)acetamide 
• 174727-79-8 1-(2,5-Dimethyl-benzyl)-2-methyl-1H-indole-3-carbaldehyde 
• 70477-49-5 Thiocyanatomethyl-2,5-dimethylbenzol 
• 13544-84-8 2,5-dimethylbenzyl triphenylphosphonium chloride 
• 98237-17-3 1-(2,5-Dimethylbenzyl)-isochinolin 
• 107416-10-4 2,2-Dimethyl-3-(2,5-dimethyl-phenyl)-propionamid 
• 107414-95-9 1,1-Dimethyl-2-<2,5-dimethyl-phenyl>-aethylisocyanat 
• 105254-11-3 2,5,α,α-Tetramethyl-phenaethylamin 
• 1357168-56-9 N-[3-(2,5-dimethylbenzyloxy)-4-(N-methanesulfonyl-N-methylamino)phenyl]-3,5-bis(trifluoromethyl)benzamide 
• 1357168-57-0 N-[3-(2,5-dimethylbenzyloxy)-4-(N-methanesulfonyl-N-methylamino)phenyl]-3-bromobenzamide 
• 1357168-58-1 N-[3-(2,5-dimethylbenzyloxy)-4-(N-methanesulfonyl-N-methylamino)phenyl]-4-chlorobenzamide 

Relevant articles and documents

Improved preparation method for 2,5-disubstituted benzyl chloride

The invention relates to an improved preparation method for 2,5-disubstituted benzyl chloride. The improved preparation method is characterized in that the 2,5-disubstituted benzyl chloride is prepared through a reaction as described in the specification. In the reaction, R and R each independently represent a C1-10 alkyl group, preferably a C1-6 alkyl group, and most preferably a methyl group. The method comprises the following steps: reacting paraformaldehyde with concentrated hydrochloric acid, adding p-disubstituted benzene, carrying out gradient heating, conducting heating to 50-65DEG C at first, carrying out reacting at the temperature for 1-3 hours, then conducting heating to 75-90 DEG C, and carrying out reacting for 6-10 hours at the temperature.

Method for preparing 2, 5-dimethylphenylacetyl chloride

The invention discloses a method for preparing 2, 5-dimethylphenylacetyl chloride, and belongs to the field of pesticide intermediate synthesis. According to the method, p-xylene is used as an initialraw material, chloromethylation, cyaniding, hydrolysis and acylating chlorination are carried out, 2, 5-dimethylphenylacetyl chloride is obtained after continuous reaction without purification, the total yield of the four steps of reaction is 75%, and the product purity is greater than 99.0%. The method is simple in process and only needs to purify the final product and is low in operation cost,mild in reaction condition and high in yield and product purity and is very easy to realize industrial production.

Ir-Catalyzed Asymmetric and Regioselective Hydrogenation of Cyclic Allylsilanes and Generation of Quaternary Stereocenters via the Hosomi-Sakurai Allylation

A number of cyclic dienes containing the allylsilane moiety were prepared by a Birch reduction and subjected to iridium-catalyzed regioselective and asymmetric hydrogenation, which provided chiral allylsilanes in high conversion and enantiomeric excess (up to 99 % ee). The compounds were successively used in the Hosomi–Sakurai allylation with various aldehydes employing TiCl4 as Lewis acid, providing adducts with two additional stereogenic centers in excellent diastereoselectivity.

METHOD FOR PREPARING 2,5-DIMETHYLPHENYLACETIC ACID

Provided is a method for preparing 2,5-dimethylphenylacetic acid, wherein p-xylene is mixed with paraformaldehyde and concentrated hydrochloric acid in a solvent of ion liquid to obtain 2,5-dimethyl benzyl chloride by the chloromethylation reaction. Then, 2,5-dimethyl benzyl chloride is introduced into a reactor with an acid binding agent and a solvent, the carbonylation and hydrolysis reaction is conducted in the presence of a catalyst to obtain 2,5-dimethylphenylacetic acid. The present process has new route, less synthesis steps, simple operation, lower cost, increased yield, and is friendly to the environment. Therefore, the method is suitable for industrial production.

A METHOD FOR PREPARING 2,5-DIMETHYLPHENYLACETIC ACID

Provided is a method for preparing 2,5-dimethylphenylacetic acid, wherein p-xylene is mixed with paraformaldehyde and concentrated hydrochloric acid in a solvent of ion liquid to obtain 2,5-dimethyl benzyl chloride by the chloromethylation reaction. Then, 2,5-dimethyl benzyl chloride is introduced into a reactor with an acid binding agent and a solvent, the carbonylation and hydrolysis reaction is conducted in the presence of a catalyst to obtain 2,5-dimethylphenylacetic acid. The present process has new route, less synthesis steps, simple operation, lower cost, increased yield, and is friendly to the environment. Therefore, the method is suitable for industrial production.

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.

Condensation reactions of planar chiral tricarbonyl-chromium-complexed benzylic alcohols and acetates with reactive arenes

The condensation reaction of planar chiral 2- and 2,5-substituted tricarbonyl-chromium complexed benzylic alcohols and acetates with reactive arenes (durene, anisole, 1,3-dimethoxybenzene, diphenyl ether) is reported. The reactions were performed in both racemic and enantiomeric versions, optically pure and S-(-)-[2-methoxybenzyl alcohol]-tricarbonyl-chromium being prepared by LiAlH4 reduction of diastereomeric, t.l.c. separated, (-)-menthyl esters of [2-methoxybenzoic acis]-tricarbonyl-chromium. The condensation of the difunctional complex [1,4-diacetoxymethylene-2,5-dimethoxybenzene]-tricarbonyl- chromium with an excess of anisole proved the same reactivity at both reactive benzylic sites thus serving as a model for possible polycondensation process. Corresponding optically pure difunctional starting complexes were obtained by t.l.c. separation of diasteromeric diesters with R-(-)-lactic or S-(-)-mandelic acids.

An inexpensive and convenient procedure for chloromethylation of aromatic hydrocarbons by phase transfer catalysis in aqueous media

Reaction of aromatic hydrocarbons catalyzed by a novel catalytic system consisting of zinc chloride, acetic acid, sulfuric acid and PEG-800 in aqueous media under PTC conditions results in chloromethylation in good to excellent yield.

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.

Paracyclophanes. Part 58 [1]. On the use of the stilbene-phenanthrene photocyclization in [2.2]paracyclophane chemistry

The application of the stilbene→phenanthrene photocyclization to [2.2]paracyclophane chemistry has been investigated. For the model system 4-styryl[2.2]paracyclophane (2) to [2.2]phenanthrenoparacyclophane (3) the reaction allows the introduction of alkyl substituants in the 6-, 7-, 8- and 9-position of the phenanthrene moiety. However, when the substituent in the 9-position (bay area of phenanthrene nucleus) becomes too large, viz. tert-butyl, no ring closure is observed anymore. The side products of the process (ring cleavage products of the cyclophane core such as 9 and 10) have been characterized for the first time. Extension of the condensed deck is possible leading to PAH-phanes as demonstrated by the preparation of the chrysenophanes 45 and 60; the cyclization to novel helicenophanes such as 50 also takes place without difficulties. In the case of 1,2-di(4-[2.2] paracyclophanyl)ethene (63) the triply-layered hydrocarbon 65 is produced on irradiation in small amounts.