552-45-4

Basic information

• Product Name: 2-Methylbenzyl chloride
• Synonyms: MBC;A-CHLORO-O-XYLENE;AKOS BBS-00003859;ALPHA-CHLORO-O-XYLENE;2-METHYLBENZYL CHLORIDE;1-(CHLOROMETHYL)-2-METHYLBENZENE;1-(chloromethyl)-2-methyl-benzen;2-(Chloromethyl)toluene
• CAS NO: 552-45-4
• Molecular Formula: C₈H₉Cl
• Molecular Weight: 140.61
• EINECS: 209-013-8
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 552-45-4.mol
• Article Data: 31

Chemical Properties

• Melting Point: -2 °C
• Boiling Point: 197-199 °C(lit.)
• Flash Point: 165 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.063 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.541(lit.)
• Storage Temp.: 0-6°C
• Solubility: soluble in Ether
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, bases, alcohols, amines. Corrodes steel.
• Merck: 14,10091
• BRN: 386016
• CAS DataBase Reference: 2-Methylbenzyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylbenzyl chloride(552-45-4)
• EPA Substance Registry System: 2-Methylbenzyl chloride(552-45-4)

Safety Data

• Hazard Codes: C,Xn
• Statements: 34-36/37/38-22
• Safety Statements: 26-36/37/39-45-37/39
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 2
• F: 19
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 552-45-4(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

General Description

A colorless to pale-yellow colored liquid with a pungent odor. Insoluble in water. Slightly denser than water. Flash point 165°F. Contact may irritate skin, eyes, and mucous membranes. May be toxic by ingestion. Used to make other chemicals.

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

• 50-00-0 formaldehyd 
• 64-19-7 acetic acid 
• 108-88-3 toluene 
• 95-47-6 o-xylene 
• 107-30-2 chloromethyl methyl ether 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 7782-50-5 chlorine 
• 56-23-5 tetrachloromethane 
• 7791-25-5 sulfuryl dichloride 
• 94-36-0 dibenzoyl peroxide 
• 542-88-1 bis(2-chloromethyl)ether 
• 932-31-0 ortho-tolylmagnesium bromide 

Downstream Products

• 98237-15-1 1-(2-Methylbenzyl)-isochinolin 
• 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 
• 149289-01-0 4-(2-methyl-benzyloxy)-benzoic acid 
• 13209-15-9 1,2-bis(dibromomethyl)benzene 
• 529-20-4 2-methylphenyl aldehyde 

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.

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.

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.