3-S-Isothiuronium propyl sulfonate
[CAS# 21668-81-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonic acid / sulfinic acid
• Name: 3-S-Isothiuronium propyl sulfonate
• Synonyms: 3-[(Aminoiminomethyl)thio]-1-propanesulfonic acid
• Molecular Formula: 2(C₄H₁₀N₂S)^.H₂SO₄
• Molecular Weight: 334.48
• CAS Registry Number: 21668-81-5
• EC Number: 244-520-8
• SMILES: C(CSC(=N)N)CS(=O)(=O)O

Properties

• Melting point: 254-256 ºC

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H312-H314-H317-H412
• Precautionary Statements: P260-P261-P264-P270-P272-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P333+P317-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H312
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314

Discovory and Applicatios

3-S-Isothiuronium propyl sulfonate is a sulfur-containing compound featuring a propyl sulfonate backbone and an isothiuronium functional group. This compound has been explored for its ability to act as a thiolating agent and its unique role in various organic synthesis reactions. The discovery of 3-S-Isothiuronium propyl sulfonate stemmed from research into the synthesis of sulfur-based intermediates that could be used for the modification of biomolecules and the preparation of specialty chemicals.

The isothiuronium group in this molecule plays a critical role in its chemical reactivity. This group contains sulfur, which can facilitate the introduction of thiol groups into organic frameworks through nucleophilic substitution reactions. The thiolation process is important in many industrial and pharmaceutical applications, where the presence of sulfur atoms can significantly influence the properties of the final product, such as improving thermal stability and resistance to oxidation.

One of the key applications of 3-S-Isothiuronium propyl sulfonate is in the field of bioconjugation, where it is used to introduce thiol groups into proteins and other biomolecules. This modification allows for the further attachment of other molecules or functional groups through disulfide bond formation. Such thiol-modified biomolecules are used in drug development, as well as in diagnostic applications, where they enable the binding of specific markers or therapeutic agents to target proteins.

In the realm of material science, 3-S-Isothiuronium propyl sulfonate has been utilized as a crosslinking agent in the synthesis of polymers and hydrogels. The introduction of sulfur-containing groups enhances the chemical stability and durability of these materials, making them more resistant to environmental degradation. This has been particularly valuable in the production of advanced coatings and adhesives, where the incorporation of sulfur groups leads to improved adhesion and mechanical properties.

In addition, the sulfonate group in 3-S-Isothiuronium propyl sulfonate provides water solubility, which is advantageous in aqueous-phase reactions. This solubility enhances its applicability in biological environments and in industrial processes that require water-compatible reagents. The compound's reactivity, combined with its versatility in both organic and aqueous media, has led to its widespread use in synthetic chemistry, materials science, and biotechnology.