PROPYL P-TOLUENESULFONATE Chemical Properties

Melting point:

<-20 °C

Boiling point:

140 °C (2 mmHg)

Density 

1.15

refractive index 

1.5065-1.5085

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Liquid

color 

Clear light yellow

InChI

InChI=1S/C10H14O3S/c1-3-8-13-14(11,12)10-6-4-9(2)5-7-10/h4-7H,3,8H2,1-2H3

InChIKey

JTTWNTXHFYNETH-UHFFFAOYSA-N

SMILES

C1(S(OCCC)(=O)=O)=CC=C(C)C=C1

CAS DataBase Reference

599-91-7

EPA Substance Registry System

Benzenesulfonic acid, 4-methyl-, propyl ester (599-91-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26

HS Code 

29041000

MSDS

• Language:English Provider:ACROS

PROPYL P-TOLUENESULFONATE Usage And Synthesis

Chemical Properties

clear light yellow liquid

Uses

Propyl 4-Toluenesulfonate is used as a catalyst for epoxy resins and amine compositions. Propyl 4-Toluenesulfonate is also used in soldering of electronic parts.

Synthesis

1. Install a thermometer and set up magnetic stirring in a 100mL three-neck flask. Add 20 mL of dichloromethane and cool the reaction flask in an ice bath to an internal temperature of 0-5°C. 2. p-Toluenesulfonic acid monohydrate (380.44 mg, 2.0 mmol), bis(trichloromethyl)carbonate (236 mg, 0.80 mmol, 0.40 equiv), and potassium phosphate trihydrate (K3PO4-3H2O, 1.38 g, 6 mmol, 3 equiv) were added to the reaction flask sequentially, and the flask was stirred for 5 minutes. 3. Two drops of triethylamine (~20 mg, 0.10 equiv) were added dropwise to the reaction vial and after bubbles were observed, the ice bath was removed and the reaction mixture was allowed to warm up to room temperature. Stirring was continued for 20 minutes. 4. n-Propanol (120.2 mg, 2.0 mmol), triethylamine (202.4 mg, 2.0 mmol) and trimethylamine hydrochloride (13.1 mg, 0.2 mmol) were added sequentially and the mixture was stirred for 30 min at room temperature. The reaction process was monitored by TLC. 5. Upon completion of the reaction, the reaction mixture was filtered and the filter cake was washed with 5 mL of dichloromethane to remove unreacted salt. 6. The filtrate was concentrated to dryness under reduced pressure to give 386 mg of propyl p-toluenesulfonate (yield: 90%).

References

[1] Patent: KR2015/67792, 2015, A. Location in patent: Paragraph 0026; 0027

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