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Methyl p-toluenesulfonate

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Methyl p-toluenesulfonate Basic information

Product Name:
Methyl p-toluenesulfonate
Synonyms:
  • 4-methyl-benzenesulfonicacimethylester
  • Benzenesulfonicacid,4-methyl-,methylester
  • Methyl 4-methylbenzenesulfonate
  • Methyl ester of 4-methylbenzenesulfonic acid
  • Methyl para-toluenesulfonate
  • p-toluenesulfonatedemethyle
  • p-Toluolsulfonsaeure methyl ester
  • p-toluolsulfonsaeuremethylester
CAS:
80-48-8
MF:
C8H10O3S
MW:
186.23
EINECS:
201-283-5
Product Categories:
  • Building Blocks
  • Chemical Synthesis
  • Organic Building Blocks
  • Sulfur Compounds
  • Organic Building Blocks
  • Sulfur Compounds
  • Tosylates
  • bc0001
  • 80-48-8
Mol File:
80-48-8.mol
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Methyl p-toluenesulfonate Chemical Properties

Melting point:
25-28 °C(lit.)
Boiling point:
144-145 °C5 mm Hg(lit.)
Density 
1.234 g/mL at 25 °C(lit.)
vapor density 
6.45 (vs air)
vapor pressure 
1 mm Hg ( 20 °C)
refractive index 
n20/D 1.5172(lit.)
Flash point:
>230 °F
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Liquid or Low Melting Solid
color 
White to yellow
Water Solubility 
Insoluble
Sensitive 
Moisture Sensitive
BRN 
609209
LogP
1.88 at 25℃
CAS DataBase Reference
80-48-8(CAS DataBase Reference)
NIST Chemistry Reference
Benzenesulfonic acid, 4-methyl-, methyl ester(80-48-8)
EPA Substance Registry System
Benzenesulfonic acid, 4-methyl-, methyl ester (80-48-8)
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Safety Information

Hazard Codes 
C,Xn
Risk Statements 
22-34-43-40-36/37/38
Safety Statements 
26-36/37/39-45-24
RIDADR 
UN 3261 8/PG 2
WGK Germany 
3
RTECS 
XT7000000
21
Autoignition Temperature
896 °F
TSCA 
Yes
HazardClass 
8
PackingGroup 
III
HS Code 
29051900
Hazardous Substances Data
80-48-8(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 341 mg/kg

MSDS

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Methyl p-toluenesulfonate Usage And Synthesis

Chemical Properties

white to slightly yellow low melting solid. Soluble in alcohol, ether, benzene, insoluble in water. Hygroscopic.

Uses

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.

Uses

Methyl p-Toluenesulfonate can be used in the manufacture of dyes and organic synthesis, and also is the raw materials of methylation.

Preparation

Methyl p-toluenesulfonate was synthesized by the reaction of p-toluenesulfonyl chloride with methanol. Mix p-toluenesulfonyl chloride and methanol, slowly add 25% sodium hydroxide solution, control the temperature below 25 °C, stop adding alkali when the pH is 9, continue stirring for 2 hours, and leave overnight. The lower layer of reactant was taken, the upper layer was extracted with benzene, the extract was recovered with benzene and then combined with the lower layer, washed with water and 5% potassium carbonate solution in turn, dried and distilled under reduced pressure to obtain the finished product of methyl p-toluenesulfonate.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 29, p. 623, 1981 DOI: 10.1248/cpb.29.623
Synthetic Communications, 15, p. 1057, 1985 DOI: 10.1080/00397918508076842

General Description

Methyl p-toluenesulfonate is sulfonate ester present as potentially genotoxic impurity in drug substances. Kinetics of reactions of methyl p-toluenesulfonate with N,N-dimethylaniline has been investigated. It participates in selective 1-substitution reaction of tetrazole.

Hazard

Toxic by ingestion and inhalation, strongirritant to skin and eyes.

Safety Profile

Poison by ingestion and subcutaneous routes. An eye and severe skin irritant. A vesicant and skin sensitizer. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of SOx.

Purification Methods

The ester is purified by distillation in vacuo and could be crystallised from pet ether or Et2O/pet ether at low temperature. It is a powerful methylating agent, is TOXIC andis a skin irritant, so it is better to purify it by repeated distillation. [IR: Schreiber Anal Chem 21 1168 1949, Buehler et al. J Org Chem 2 167 1937, Roos et al. Org Synth Coll Vol I 145 1948, Beilstein 11 IV 247.]

Methyl p-toluenesulfonate Preparation Products And Raw materials

Raw materials

Preparation Products

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