Propargyl benzenesulfonate
[CAS# 6165-75-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester
• Name: Propargyl benzenesulfonate
• Synonyms: Prop-2-ynyl benzenesulphonate
• Molecular Formula: C₉H₈O₃S
• Molecular Weight: 196.22
• CAS Registry Number: 6165-75-9
• EC Number: 228-203-1
• SMILES: C#CCOS(=O)(=O)C1=CC=CC=C1

Properties

• Density: 1.243
• Melting point: -30 °C
• Boiling point: 140-142 °C (2 mmHg)
• Refractive index: 1.525
• Flash point: 100 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 1760

Discovery and Applications

Propargyl benzenesulfonate is an organic compound with the formula C₁₀H₉O₃S and is characterized by the presence of a propargyl group attached to a benzenesulfonate moiety. This compound is used extensively in organic synthesis due to its unique chemical properties, particularly its ability to undergo various reactions that are valuable in chemical transformations.

The discovery of propargyl benzenesulfonate is part of the broader study of sulfonate esters, which gained attention in the mid-20th century for their utility in organic synthesis. The propargyl group, known for its reactivity, was combined with the benzenesulfonate group to create a compound that could facilitate a range of chemical reactions. The synthesis typically involves the reaction of propargyl alcohol with benzenesulfonyl chloride, resulting in the formation of propargyl benzenesulfonate and hydrochloric acid as a byproduct.

Propargyl benzenesulfonate is particularly valuable as an electrophile in nucleophilic substitution reactions. In these reactions, the sulfonate group acts as a good leaving group, allowing the propargyl group to be substituted with various nucleophiles. This characteristic makes it useful in the synthesis of complex organic molecules, including pharmaceuticals and natural products. Its ability to form carbon-carbon bonds through substitution reactions is a key advantage in the construction of carbon frameworks in organic chemistry.

Another significant application of propargyl benzenesulfonate is in the development of chemical probes and sensors. The compound's reactivity allows it to be used in the synthesis of molecules that can interact with biological targets, providing insights into biochemical pathways and molecular interactions. For instance, it can be employed in the development of selective inhibitors or activators of enzyme systems, contributing to drug discovery and development.

In addition to its applications in organic synthesis and chemical probing, propargyl benzenesulfonate is also utilized in polymer chemistry. It can be used as a monomer in the synthesis of polymers with unique properties, such as high thermal stability or specific reactivity, by participating in polymerization reactions.

References

2008. Rasagiline. Pharmaceutical Substances.
URL: KD-18-0057