552-45-4 Usage
Description
2-Methylbenzyl chloride, also known as o-Toluene chloride, is an organic compound belonging to the class of aromatic compounds. It is a colorless to pale-yellow colored liquid with a pungent odor. 2-Methylbenzyl chloride is insoluble in water and slightly denser than water. It has a flash point of 165°F and may cause irritation upon contact with skin, eyes, and mucous membranes. It can be toxic if ingested and is primarily used as an intermediate in the synthesis of other chemicals.
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
Check Digit Verification of cas no
The CAS Registry Mumber 552-45-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 2 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 552-45:
(5*5)+(4*5)+(3*2)+(2*4)+(1*5)=64
64 % 10 = 4
So 552-45-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H9Cl/c1-7-4-2-3-5-8(7)6-9/h2-5H,6H2,1H3
552-45-4Relevant articles and documents
Mechanism of solvolysis of substituted benzyl chlorides in aqueous ethanol
Denegri, Bernard,Mati?, Mirela,Va?ko, Monika
supporting information, (2021/11/22)
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
Zheng, Dagui,Mao, Liu-Liang,Zhu, Xian-Hong,Zhou, An-Xi
supporting information, p. 2793 - 2800 (2018/11/06)
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
Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
supporting information, p. 10145 - 10149 (2016/08/16)
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.
