PROPARGYL BENZENESULFONATE Chemical Properties

Melting point:

−30 °C(lit.)

Boiling point:

140-142 °C2 mm Hg(lit.)

Density 

1.243 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.525(lit.)

Flash point:

213 °F

storage temp. 

2-8°C

form 

liquid

Appearance

Light brown to brown Liquid

BRN 

1107228

InChI

InChI=1S/C9H8O3S/c1-2-8-12-13(10,11)9-6-4-3-5-7-9/h1,3-7H,8H2

InChIKey

RAGBYXLIHQFIPK-UHFFFAOYSA-N

SMILES

C(OS(C1=CC=CC=C1)(=O)=O)C#C

CAS DataBase Reference

6165-75-9(CAS DataBase Reference)

EPA Substance Registry System

2-Propyn-1-ol, 1-benzenesulfonate (6165-75-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 1760 8/PG 2

WGK Germany 

3

F 

10

HazardClass 

8

PackingGroup 

III

HS Code 

2905299090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

PROPARGYL BENZENESULFONATE Usage And Synthesis

Uses

Propargyl Benzenesulfonate is a general chemical reagent used in organic syntheses. Used in the manufacture of Omarigliptin, a DPP-4 inhibitor used in the treatment of type-2 diabetes.

Synthesis

The general procedure for the synthesis of propargylbenzenesulfonic acid from 2-propyn-1-ol and benzenesulfonyl chloride is as follows: 1.0 mol of 2-propyn-1-ol and 500 mL of methylene chloride were added to a reaction flask, and triethylamine was added as a base under stirring conditions. The reaction mixture was cooled to below 15°C and 2.1 mol of benzenesulfonyl chloride was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was allowed to gradually warm up to room temperature and stirring was continued for 1 hour. Subsequently, the reaction temperature was raised to reflux and the reaction was continued for 2 hours. The progress of the reaction was monitored by gas chromatography and after confirming the completion of the reaction, the reaction mixture was cooled in an ice bath and left to stratify. The organic layer was separated and concentrated to obtain the crude product. The crude product was purified by recrystallization to give 187.77 g of propargyl benzenesulfonic acid in pure form. The yield of the reaction was calculated to be 95.8%, the purity of the product was 99.93%, the moisture content was 28 ppm and the acid value was 36 ppm.

References

[1] Patent: CN107840812, 2018, A. Location in patent: Paragraph 0028; 0029; 0031
[2] Patent: US2340701, 1941,
[3] Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 65
[4] J. Gen. Chem. USSR (Engl. Transl.), 1963, vol. 33, p. 647 - 650
[5] Zhurnal Obshchei Khimii, 1963, vol. 33, # 2, p. 653 - 657

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