824-55-5

Basic information

• Product Name: 2,4-DIMETHYLBENZYL CHLORIDE
• Synonyms: 1-(chloromethyl)-2,4-dimethyl-benzen;2,4-Dimethyl-1-(chloromethyl)benzene;Benzene, 1-(chloromethyl)-2,4-dimethyl-;4-(CHLOROMETHYL)-M-XYLENE;1-CHLOROMETHYL-2,4-DIMETHYLBENZENE;2,4-DIMETHYLBENZYL CHLORIDE;TIMTEC-BB SBB005790;2,4-Dimethylbenzyl chloride, GC 97%
• CAS NO: 824-55-5
• Molecular Formula: C₉H₁₁Cl
• Molecular Weight: 154.64
• EINECS: 212-531-7
• Mol File: 824-55-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: -43.35°C (estimate)
• Boiling Point: 103 °C (15 mmHg)
• Flash Point: 96°C
• Appearance: /
• Density: 1.06
• Vapor Pressure: 0.216mmHg at 25°C
• Refractive Index: 1.5375-1.5395
• BRN: 742366
• CAS DataBase Reference: 2,4-DIMETHYLBENZYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIMETHYLBENZYL CHLORIDE(824-55-5)
• EPA Substance Registry System: 2,4-DIMETHYLBENZYL CHLORIDE(824-55-5)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 45-36/37/39-25
• RIDADR: 3265
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 824-55-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Synthesis Reference(s)

The Journal of Organic Chemistry, 7, p. 6, 1942 DOI: 10.1021/jo01195a002

InChI:InChI=1/C9H11Cl/c1-7-3-4-9(6-10)8(2)5-7/h3-5H,6H2,1-2H3

Upstream product

• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 108-38-3 m-xylene 
• 7732-18-5 water 
• 51421-20-6 (2,4-dimethyl-benzyl)-hydrazine 
• 95-63-6 1,2,4-Trimethylbenzene 
• 611-01-8 2,4-dimethyl-benzoic acid 
• 89-74-7 2,4-dimethylacetophenone. 
• 95-68-1 2,4-Xylidine 
• 23617-71-2 2,4-dimethyl-benzoic acid methyl ester 
• 583-70-0 1-bromo-2,4-dimethylbenzene 
• 16054-72-1 Bis-(2,4-dimethylbenzyl)-ether 
• 7093-91-6 chloromethyl isocyanate 

Downstream Products

• 32588-46-8 bis-(2,4-dimethyl-phenyl)methane 
• 50400-99-2 N-(2,4-dimethyl-benzyl)-aniline 
• 94314-70-2 Thiocarbamidsaeure-S-<2,4-dimethyl-benzylester> 
• 54759-18-1 1-Phenoxy-4-[(2',4'-dimethyl)-benzyloxy]benzene 
• 19444-24-7 α-Hydroxy-isobuttersaeure-2,4-dimethyl-benzylester 
• 52804-02-1 Ethyl-2-(2.4-dimethylbenzyloxy)-3-methoxycinnamat 
• 110050-93-6 <2,2-Dimethyl-3-(2,4-dimethyl-phenyl)-propionyl>-benzol 
• 5612-56-6 (2,4-dimethyl-benzyl)-malonic acid 
• 52803-85-7 Methyl-2-(2.4-dimethylbenzyloxy)benzoat 
• 90535-40-3 4-mercaptomethyl-m-xylene 
• 59606-79-0 5-chloro-1-chloromethyl-2,4-dimethylbenzene 
• 78831-87-5 2,4-dimethylbenzyl bromide 
• 2735-07-1 1,2,4-tris-chloromethyl-benzene 
• 94143-65-4 1,2-bis(2,4-dimethylphenyl)ethane 

Relevant articles and documents

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.

Aromatic cation activation: Nucleophilic substitution of alcohols and carboxylic acids

A new method for the nucleophilic substitution of alcohols and carboxylic acids using aromatic tropylium cation activation has been developed. This article reports the use of chloro tropylium chloride for the rapid generation of alkyl halides and acyl chlorides under very mild reaction conditions. It demonstrates, for the first time, the synthetic potential of tropylium cations in promoting chemical transformations.

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.