552-45-4

Usage

Uses

Used in Chemical Synthesis:
2-Methylbenzyl chloride is used as a chemical intermediate for the production of various organic compounds. Its aromatic structure and reactivity make it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Methylbenzyl chloride is used as a key intermediate in the synthesis of various drugs. Its ability to form a wide range of derivatives allows for the development of new drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
2-Methylbenzyl chloride is also utilized in the agrochemical industry for the production of pesticides and other crop protection agents. Its chemical properties enable the creation of compounds that can effectively control pests and diseases in agriculture.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 2-Methylbenzyl chloride serves as a starting material for the synthesis of various dyes and pigments. Its aromatic structure allows for the development of colorants with specific properties, such as lightfastness and stability.
Used in Polymer Industry:
2-Methylbenzyl chloride is employed in the polymer industry as a monomer for the production of specialty polymers. These polymers can be used in various applications, including coatings, adhesives, and elastomers, due to their unique properties.

Air & Water Reactions

Because of its insolubility 2-Methylbenzyl chloride doesn't react vigorously with water, although 2-Methylbenzyl chloride does generate annoying levels of hydrogen chloride fumes.

Reactivity Profile

2-Methylbenzyl chloride is rapidly decomposed when heated in the presence of iron.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C8H9Cl/c1-7-4-2-3-5-8(7)6-9/h2-5H,6H2,1H3

Upstream product

• 128-09-6 N-chloro-succinimide 
• 95-47-6 o-xylene 
• 89-95-2 2-methyl-benzyl alcohol 
• 50-00-0 formaldehyd 
• 64-19-7 acetic acid 
• 108-88-3 toluene 
• 63246-55-9 2-methyl-benzylium 
• 75366-04-0 2-methyl-1H-cyclopropabenzene 
• 88531-10-6 2-Methyl-1-trichloromethyl-cyclohexanol 
• 7093-91-6 chloromethyl isocyanate 
• 107-30-2 chloromethyl methyl ether 
• 38870-89-2 Methoxyacetyl chloride 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 

Downstream Products

• 36995-46-7 4-[(2-methylphenyl)methyl]pyridine 
• 36995-45-6 2-[(2-methylphenyl)methyl]pyridine 
• 98237-15-1 1-(2-Methylbenzyl)-isochinolin 
• 142087-14-7 1-(2-methyl-benzyl)-1H-benzo[d][1,2,3]triazole 
• 321904-28-3 2-(2-methylbenzyl)cyclohexanone 
• 6619-57-4 diethyl 2-(2-methylbenzyl)-malonate 
• 222612-91-1 2-methylbenzyl 4-methylbenzyl sulfide 
• 141538-50-3 N-methyl-N-(2-methylbenzyl)-4-methylbenzylamine 
• 876476-21-0 methyl-(2-methyl-benzyl)-(3-methyl-benzyl)-amine 
• 38418-11-0 2-methylbenzyl benzoate 
• 52086-50-7 diethyl 2-methyl-2-(2-methylbenzyl)malonate 
• 222612-88-6 (2?methylbenzyl)benzyl sulfide 
• 10479-23-9 benzyl-methyl-(2-methyl-benzyl)-amine 
• 54636-44-1 3-phenyl-4-o-tolyl-butan-2-one 

Relevant academic research and scientific papers

Mechanism of solvolysis of substituted benzyl chlorides in aqueous ethanol

The mechanism of solvolyses of activated ortho-, meta- and para-substituted benzyl chlorides in aqueous ethanol has been studied by using the Hammett-Brown and Yukawa-Tsuno treatments as well as by correlating logarithms of solvolysis rate constants with relative stabilities of corresponding benzyl carbocations in water calculated at the IEFPCM-M06–2X/6-311+G(3df,3pd) level of theory. Benzyl chlorides containing strong conjugative electron-donors in the para-position solvolyze by the SN1 mechanism, whereas other activated benzyl chlorides solvolyze by the SN2 mechanism via loose transition states.

Synthesis method of 3-isochromanone

The invention belongs to the technical field of synthesis of organic intermediates, and particularly relates to a synthesis method of 3-isochromanone, which comprises the following steps of: (1) synthesizing o-methyl benzyl chloride by using o-xylene as a raw material; (2) synthesizing o-methyl benzyl cyanide by taking o-methyl benzyl chloride as a raw material; (3) synthesizing sodium o-methyl phenylacetate by taking o-methyl benzyl cyanide as a raw material; (4) synthesizing o-methyl phenylacetic acid by taking sodium o-methyl phenylacetate as a raw material; (5) synthesizing 2-chloromethylphenylacetic acid by taking o-methyl phenylacetic acid as a raw material; and (6) synthesizing 3-isochromanone by taking 2-chloromethyl phenylacetic acid as a raw material. The synthesis method of 3-isochromanone has the advantages of simple reaction process, easily available raw materials, mild reaction conditions, high product yield, low production cost, high yield, high product purity, good quality, low production waste discharge amount and the like, the product purity is greater than or equal to 99.5%, the production yield is greater than or equal to 92%, and the product meets the use requirements of foreign high-end users.

NMP-mediated chlorination of aliphatic alcohols with aryl sulfonyl chloride for the synthesis of alkyl chlorides

NMP-mediated chlorination of aliphatic alcohols has been developed for the synthesis of alkyl chlorides. This facile, efficient and practical approach used simple and readily available aryl sulfonyl chlorides as the chlorination reagent for the construction of C–Cl bond in good to excellent yields with mild conditions and broad substrate scope.

Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers

A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.

Improved Halogenation of Methyl Aromatics and Methyl Heteroaromatics: Unexpected Reactivity of Tetrahalogeno-diphenylglycolurils

1,3,4,6-Tetrachloro (TCDGU) and 1,3,4,6-tetrabromo-3α,6α-diphenylglycolurils smooth halogen oxidizers have been exploited in a new direction as reagents for free radical substitution toward some N-halosuccinimide nonreactive bis-heterocycles. An unexpected selectivity and reactivity were observed with methyl benzenes, methyl heterocycles, and methyl-bis-heterocycles of interest. A chemometric study has been performed to optimize five independent factors of the chlorination reaction with TCDGU. The predictive model was established either for the halogenation conversion and the ratio of monochlorination.

Iron catalyzed halogenation of benzylic aldehydes and ketones

A simple and efficient iron-catalyzed method for chlorination of aromatic carbonyl compounds is reported. By using 4-10 mol% Fe(iii) oxo acetate catalyst, prepared by solid state atmospheric oxidation of Fe(ii) acetate, in combination with triethylsilane and chlorotrimethylsilane, hydrosilylation of benzylic carbonyl compounds with subsequent chlorination is achieved within a few hours at room temperature. This new method is mild and rapid compared to the conventional two step approach involving reduction and chlorination reactions in separate stages. Development of synthetic methodology is also supplemented here by kinetic investigation of the reaction mechanism, which supports the tentative mechanisms suggested previously for similar reactions. This journal is

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 organic transformations mediated by ZrOCl28H 2O in Water

Operationally simple and environmentally benign methods for some organic transformations comprising reductive coupling of sulfonyl chlorides, chemoselective deoxygenation of sulfoxides, and halogenation of alcohols mediated by ZrOCl28H2O/MX in water have been developed.

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.

A novel synthesis of tolunitriles by selective ammoxidation

A new approach to synthesize tolunitriles is reported. Tolunitriles can be prepared by selective ammoxidation of methylbenzyl chlorides prepared by chloromethylation of toluene. The total yields can reach 83% and the selectivity of tolunitriles is almost 100%. This approach provides a new path for preparing alkylbenzonitriles and other aromatic nitriles.