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Methyl tosylate

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Identification
Molecular formula
C8H10O3S
CAS number
80-48-8
IUPAC name
methyl 4-methylbenzenesulfonate
State
State

At room temperature, methyl tosylate is typically a liquid.

Melting point (Celsius)
-29.00
Melting point (Kelvin)
244.15
Boiling point (Celsius)
164.00
Boiling point (Kelvin)
437.15
General information
Molecular weight
186.22g/mol
Molar mass
186.2220g/mol
Density
1.2200g/cm3
Appearence

Methyl tosylate is a colorless to pale yellow liquid with a slightly sweet aromatic odor. It is commonly used as an intermediate in organic synthesis.

Comment on solubility

Solubility of Methyl 4-Methylbenzenesulfonate

Methyl 4-methylbenzenesulfonate, with the chemical formula C9H10O3S, exhibits intriguing solubility characteristics. Understanding the solubility of this compound can be quite insightful for various applications. Here are key points to consider:

  • Polarity: The presence of the sulfonate group enhances the polarity of the molecule, contributing to its ability to interact with polar solvents.
  • Solvent Compatibility: Methyl 4-methylbenzenesulfonate is typically soluble in polar organic solvents such as methanol, ethanol, and acetone, whereas its solubility in non-polar solvents like hexane is quite limited.
  • Hydrogen Bonding: The sulfonate group can participate in hydrogen bonding, which can further facilitate solubility in polar environments.
  • Practical Usage: Due to its solubility in various solvents, it is often used in organic synthesis and chemical reactions that require a soluble reagent.

In summary, the solubility of methyl 4-methylbenzenesulfonate is primarily influenced by its molecular structure, specifically the polar sulfonate group that allows for favorable interactions with polar solvents, making it a versatile compound in chemical processes.

Interesting facts

Interesting Facts about Methyl 4-Methylbenzenesulfonate

Methyl 4-methylbenzenesulfonate, often referred to as a sulfonate ester, is a fascinating compound with various intriguing applications and characteristics. Here are some key points to consider:

  • Versatile Reactivity: This compound is known for its reactivity in organic synthesis. Its sulfonate group makes it an excellent leaving group in nucleophilic substitution reactions.
  • Intermediate in Synthesis: Methyl 4-methylbenzenesulfonate serves as an important intermediate for the synthesis of various pharmaceuticals and agrochemicals. 
  • Environmental Stability: The compound demonstrates a level of environmental stability, which can be beneficial or a concern, depending on the context of its usage.
  • Accordion Effect in Chemistry: It exemplifies the concept of the "accordion effect," where slight changes in the substitution can dramatically influence the compound's properties and reactivity.
  • Research Applications: Researchers are exploring its potential uses in developing new materials and advanced intermediates due to its unique structure.
  • Industrial Relevance: Its application extends beyond academic chemistry; the compound finds uses in industries such as cosmetics, where sulfonate esters often serve as surfactants.

In summary, methyl 4-methylbenzenesulfonate is not just a chemical compound; it's a gateway to fascinating research and practical applications in a variety of fields. As a chemist or a student, understanding its properties helps one appreciate the broader implications it holds in both synthetic chemistry and industrial practices.

Synonyms
Methyl p-toluenesulfonate
80-48-8
Methyl 4-methylbenzenesulfonate
Methyl tosylate
Methyl-p-toluenesulfonate
Methyl toluene-4-sulfonate
Methyl p-tosylate
Methyl toluene-4-sulphonate
Benzenesulfonic acid, 4-methyl-, methyl ester
p-Toluenesulfonic acid, methyl ester
Methyl para-toluenesulfonate
methyl 4-methylbenzene-1-sulfonate
Methyl toluene sulfonate
METHYL P-METHYLBENZENESULFONATE
Methyl 4-toluene sulfonate
p-Toluenesulfonic acid methyl ester
p-Methylbenzenesulfonate methyl ester
CCRIS 9151
p-Toluolsulfonsaeure methyl ester
HSDB 2025
ortho-Toluenesulfonic acid, methyl ester
Methyl 4-toluenesulfonate
EINECS 201-283-5
4-Toluenesulfonic acid, methyl ester
UNII-4SU69KI68L
Methylester kyseliny p-toluensulfonove
NSC 406335
BRN 0609209
DTXSID4052550
AI3-02550
toluene-4-sulfonic acid methyl ester
NSC-406335
Methyl-(4)-toluenesulfonate
4SU69KI68L
DTXCID1031123
Methyl-d3 4-Methylbenzenesulfonate
4-11-00-00247 (Beilstein Handbook Reference)
p-methylbenzenesulfonic acid methyl ester
4-methyl-benzenesulfonic acid methyl ester
METHYL 4-TOLUENE SULFONATE [HSDB]
Methyl ester of 4-methylbenzenesulfonic acid
MFCD00069406
MFCD00008417
methyltosylate
tosome
methyl tosylat
p-Toluolsulfonsaeure methyl ester [German]
Methyl ptosylate
Methyl 4-methylbenzenesulphonate
Methylester kyseliny p-toluensulfonove [Czech]
MeOTs
TsOMe
tosylate methyl ester
Methylptoluenesulfonate
Methyl ptoluenesulfonate
methyl-p-toluensulfonate
Methyl toluene4sulfonate
Methyl 4toluene sulfonate
methyl-p-toluenesulphonate
Methyl p-toluenesulphonate
methyl paratoluenesulfonate
methyl p-toluene-sulfonate
methyl rho-toluenesulfonate
methyl-4-toluene sulfonate
Methyl p-toluene sulphonate
methyl-4-toluene sulphonate
methyl-paratoluene sulphonate
WLN: 1OSWR D1
Methyl para-toluenesulphonate
methyl para-toluene sulfonate
SCHEMBL27524
Methyl 4methylbenzenesulfonate
methyl-4-methylbenzenesulfonate
pToluolsulfonsaeure methyl ester
CHEMBL5189891
Methyl p-toluenesulfonate, 98%
paratoluen sulphonate methyl ester
((2)H1,(3)H)methyl tosylate
pMethylbenzenesulfonate methyl ester
pToluenesulfonic acid, methyl ester
4Toluenesulfonic acid, methyl ester
STR01542
Methylester kyseliny ptoluensulfonove
p-toluene sulfonic acid methyl ester
Tox21_303790
NSC406335
p-toluene-sulphonic acid methyl ester
toluene-4-sulfonic acid-methyl ester
AKOS008938769
FM11154
CAS-80-48-8
NCGC00357078-01
SY276580
Benzenesulfonic acid, 4methyl, methyl ester
DB-020470
CS-0015899
NS00019688
T0269
EN300-15726
D72514
Methyl p-toluenesulfonate, purum, >=97.0% (GC)
Q25616437
F0001-2085