Ethanesulfonyl chloride
[CAS# 594-44-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonyl halide
• Name: Ethanesulfonyl chloride
• Molecular Formula: C₂H₅ClO₂S
• Molecular Weight: 128.57
• CAS Registry Number: 594-44-5
• EC Number: 209-842-5
• SMILES: CCS(=O)(=O)Cl

Properties

• Density: 1.357
• Boiling point: 177 °C
• Refractive index: 1.452-1.454
• Flash point: 83 °C
• Water solubility: DECOMPOSES

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H302-H311-H312-H314-H330-H335
• Safety Statements: P260-P261-P262-P264-P270-P271-P280-P284-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P319-P320-P321-P330-P361+P364-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	1	H330
Acute toxicity	Acute Tox.	2	H310
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	1	H310
Acute toxicity	Acute Tox.	4	H332
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314
Germ cell mutagenicity	Muta.	2	H341
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

• Transport Information: UN 2927

Discovery and Applications

Ethanesulfonyl chloride is an important reagent in organic chemistry, known for its reactivity and applications in various synthetic processes. This compound consists of an ethyl group attached to a sulfonyl chloride functional group, which confers high reactivity, especially in nucleophilic substitution reactions. Ethanesulfonyl chloride has found widespread use as a sulfonylating agent in the preparation of sulfonates, sulfones, and sulfonamides, making it invaluable in the pharmaceutical, agrochemical, and polymer industries.

The discovery of ethanesulfonyl chloride dates back to the mid-20th century when chemists were exploring organosulfur compounds for their synthetic potential. Sulfonyl chlorides, such as ethanesulfonyl chloride, were identified as highly reactive intermediates that could introduce sulfonyl groups into various molecules. The sulfonyl chloride group (-SO2Cl) readily reacts with nucleophiles such as alcohols, amines, and thiols, making ethanesulfonyl chloride a key reagent in the synthesis of a wide array of compounds.

One of the primary applications of ethanesulfonyl chloride is in the formation of sulfonates, which are valuable intermediates in both organic synthesis and industrial applications. Sulfonates are typically formed when ethanesulfonyl chloride reacts with alcohols, resulting in the formation of sulfonate esters. These compounds are widely used as intermediates in the synthesis of pharmaceuticals, agrochemicals, and dyes. Additionally, sulfonate esters serve as protecting groups for hydroxyl functionalities in multistep organic syntheses, offering chemists a means to selectively modify molecules.

In the pharmaceutical industry, ethanesulfonyl chloride plays a significant role in the synthesis of sulfonamide-based drugs. Sulfonamides are a class of compounds that have found application as antibiotics, diuretics, and antihypertensives, among other therapeutic uses. The reaction of ethanesulfonyl chloride with amines leads to the formation of sulfonamides, which are key pharmacophores in many drug molecules. This reactivity has made ethanesulfonyl chloride an essential tool in medicinal chemistry for the development of new therapeutics.

Ethanesulfonyl chloride is also used in the preparation of sulfones, which are important in both medicinal chemistry and material science. Sulfones are typically formed when ethanesulfonyl chloride reacts with nucleophiles such as thiols, resulting in the replacement of the chloride with a sulfonyl group. Sulfones have been used as intermediates in the synthesis of antibiotics and antifungal agents, and they also serve as building blocks for polymers and other materials with high thermal and chemical stability.

In the field of agrochemicals, ethanesulfonyl chloride is used to synthesize herbicides and pesticides. Its reactivity allows for the introduction of sulfonyl functional groups into compounds that can inhibit the growth of weeds or pests. These agrochemicals often exhibit high selectivity and potency, making ethanesulfonyl chloride an important reagent in the development of environmentally sustainable agricultural products.

Ethanesulfonyl chloride also finds application in the polymer industry. Sulfonyl groups, introduced via ethanesulfonyl chloride, impart desirable properties such as enhanced chemical resistance and thermal stability to polymers. This makes the compound useful in the synthesis of specialty polymers for use in harsh chemical environments or high-temperature applications.

The handling of ethanesulfonyl chloride requires caution due to its high reactivity and potential hazards. The compound is corrosive and can cause severe burns upon contact with skin or eyes. It also releases hydrochloric acid (HCl) when it reacts with water, necessitating the use of appropriate protective equipment and ventilation when working with the reagent.

In conclusion, ethanesulfonyl chloride is a versatile and valuable reagent in organic chemistry, with applications ranging from pharmaceuticals to agrochemicals and polymers. Its ability to introduce sulfonyl groups into a variety of molecules has made it a cornerstone of synthetic chemistry, enabling the development of new compounds with diverse biological and material properties.

References

2023. A novel strategy to bind pyrimidine sulfonamide derivatives with odd even chains: exploration of their design, synthesis and biological activity evaluation. Molecular Diversity, 28(3).
DOI: 10.1007/s11030-023-10729-0

2019. A green and facile synthesis of an industrially important quaternary heterocyclic intermediates for baricitinib. BMC Chemistry, 13(1).
DOI: 10.1186/s13065-019-0639-y

2022. Synergistic effect of novel ionic liquid/graphene complex on the flame retardancy of epoxy nanocomposites. Carbon Letters, 33(2).
DOI: 10.1007/s42823-022-00440-9