Methyl p-toluenesulfonate

Base Information

• Chemical Name: Methyl p-toluenesulfonate
• CAS No.: 80-48-8
• Molecular Formula: C8H10O3S
• Molecular Weight: 186.232
• Hs Code.: 29051900
• European Community (EC) Number: 201-283-5
• NSC Number: 406335
• UNII: 4SU69KI68L
• DSSTox Substance ID: DTXSID4052550
• Nikkaji Number: J54.424H
• Wikidata: Q25616437
• Mol file: 80-48-8.mol

Synonyms:methyl 4-toluene sulfonate;methyl p-toluene sulfonate

Chemical Property of Methyl p-toluenesulfonate

Chemical Property:

• Appearance/Colour: white to slightly yellow low melting solid
• Vapor Pressure: 1 mm Hg ( 20 °C)
• Melting Point: 25-28 °C(lit.)
• Refractive Index: n20/D 1.5172(lit.)
• Boiling Point: 291.8 °C at 760 mmHg
• Flash Point: 130.3 °C
• PSA: 51.75000
• Density: 1.21 g/cm³
• LogP: 2.41090
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 186.03506535
• Heavy Atom Count: 12
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

Methyl p-Toluenesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xn
• Hazard Codes: C,Xn
• Statements: 22-34-43-40-36/37/38
• Safety Statements: 26-36/37/39-45-24

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzenesulfonic Acid Derivatives
• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC
• Uses: Methyl p-Toluenesulfonate can be used in the manufacture of dyes and organic synthesis, and also is the raw materials of methylation. Methyl p-toluenesulfonate is used as a methylating agent in organic synthesis. It acts as a catalyst for alkyd resins. It is also employed in selective 1-substitution reaction of tetrazole. Further, it is used in the preparation of dyes.

Technology Process of Methyl p-toluenesulfonate

There total 91 articles about Methyl p-toluenesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Trimethyl orthoacetate (1445-45-0) + toluene-4-sulfonic acid (104-15-4) → methyl p-toluene sulfonate (80-48-8)

Guidance literature:

at 20 ℃; for 0.5h;

Reference yield: 99.0%

methanol (67-56-1) + sodium 4-methylbenzenesulfinate (824-79-3) → methyl p-toluene sulfonate (80-48-8)

Guidance literature:

With [bis(acetoxy)iodo]benzene; at 20 ℃; for 0.25h; Reagent/catalyst;

DOI:10.3762/bjoc.14.101

Reference yield: 99.0%

methanol (67-56-1) + p-toluenesulfonyl chloride (98-59-9) → methyl p-toluene sulfonate (80-48-8)

Guidance literature:

With trimethylamine hydrochloride; triethylamine; In toluene; at 0 ℃; for 1h;

DOI:10.1002/jlcr.3231

upstream raw materials:

trans-Decalin

N-methyl-N-nitrosotoluene-p-sulfonamide

methoxybenzene

nitrobenzene

Downstream raw materials:

8,8-dimethyl-3endo-phenacyl-nortropanium; toluene-4-sulfonate

4-methyl-morpholine

1-ethyl-1-methyl-piperidinium; toluene-4-sulfonate

1-methyl-2-pyridone

Refernces

Montmorillonite clay catalyzed tosylation of alcohols and selective monotosylation of diols with p-toluenesulfonic acid: An enviro-economic route

10.1016/S0040-4020(00)00626-8

The study presents an eco-friendly and cost-effective method for the tosylation of alcohols and selective monotosylation of diols using p-toluenesulfonic acid with metal-exchanged montmorillonite clay as a catalyst. The Fe3+-montmorillonite clay demonstrated the highest effectiveness among the tested catalysts, outperforming Zn2+, Cu2+, Al3+-exchanged montmorillonites and K10 montmorillonite. This method allows for the regioselective tosylation of diols to monotosylated derivatives with high purity, favoring the primary hydroxy group in the presence of secondary hydroxy groups. The catalyst's reusability over several cycles was consistent, as shown in the tosylation of cyclohexanol. This approach minimizes by-product formation, typically just water, and offers advantages such as ease of catalyst recovery, recyclability, and enhanced stability compared to traditional methods using sulfonyl chloride or anhydride with organic bases.

Catalytic Activities of Salicylaldehyde Derivatives. VI. Syntheses of Some Dimethylsulfonio Derivatives of Salicylaldehyde

10.1246/bcsj.51.2435

The study investigates the catalytic activities of salicylaldehyde derivatives, specifically focusing on the synthesis of 3-, 4-, and 5-dimethylsulfonio derivatives of salicylaldehyde. These derivatives were prepared from corresponding bromo-2-methoxybenzylidene dibromides, bromo-o-anisaldehyde diethyl acetals, methylthio-o-anisaldehydes, and (methylthio)salicylaldehydes through a series of chemical reactions involving reagents such as sodium ethoxide, dimethyl disulfide, and methyl p-toluenesulfonate. The study also examined the racemization of L-glutamic acid catalyzed by these salicylaldehyde derivatives in the presence of copper(I) ion at pH 10 and 80°C. The results indicated that the dimethylsulfonio derivatives exhibited higher catalytic activity than known salicylaldehyde derivatives, as evidenced by their larger Hammett's constant values.

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