Dimethylsulfamoyl chloride
[CAS# 13360-57-1]

Identification

• Classification: Organic raw materials >> Organic sulfur compound
• Name: Dimethylsulfamoyl chloride
• Synonyms: N,N-Dimethylsulfamoyl chloride
• Molecular Formula: C₂H₆ClNO₂S
• Molecular Weight: 143.59
• CAS Registry Number: 13360-57-1
• EC Number: 236-412-4
• SMILES: CN(C)S(=O)(=O)Cl

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*, 1.347 g/mL Expl.)
• Index of Refraction: 1.481, Calc.^*, 1.452 (Expl.)
• Boiling Point: 186.7±9.0 ºC (760 mmHg), Calc.^*, 198.9 ºC (Expl.)
• Flash Point: 94.4 ºC, Calc.^*, 94 ºC (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS05;GHS08 Danger
• Hazard Statements: H302-H311-H312-H314-H318-H330-H350
• Precautionary Statements: P203-P260-P262-P264-P264+P265-P270-P271-P280-P284-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P318-P320-P321-P330-P361+P364-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Carcinogenicity	Carc.	1B	H350
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	1	H330
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 3390

Discovory and Applicatios

Dimethylsulfamoyl chloride is an organosulfur compound with the molecular formula C₂H₆ClNO₂S. It is classified as a sulfonamide derivative, containing both a sulfonyl (-SO₂) and a chlorosulfamoyl (-SO₂Cl) functional group. This compound is primarily used as an intermediate in organic synthesis, where its reactivity enables the formation of various sulfonamide and sulfamoyl-functionalized molecules.

The synthesis of dimethylsulfamoyl chloride has been documented in the literature as part of the development of sulfonyl chloride chemistry. It is typically prepared by the reaction of dimethylsulfamide (H₂NSO₂N(CH₃)₂) with chlorinating agents such as phosphorus oxychloride (POCl₃), thionyl chloride (SOCl₂), or phosphorus pentachloride (PCl₅). These reactions proceed under controlled conditions, often in anhydrous solvents, to facilitate selective chlorination at the sulfamoyl group. The resulting product is a colorless to pale yellow liquid or solid, depending on its purity and crystallization conditions.

Dimethylsulfamoyl chloride is widely used in pharmaceutical research and chemical synthesis. Its primary application is in the preparation of sulfonamides, which are key structural components in various drugs, agrochemicals, and functional materials. The electrophilic nature of the sulfonyl chloride group allows it to react with nucleophiles such as amines, alcohols, and thiols, forming sulfamides, sulfonylureas, and other functionalized compounds. These reactions are useful in the development of biologically active molecules, including antibacterial, antiviral, and anti-inflammatory agents.

In medicinal chemistry, sulfonamides derived from dimethylsulfamoyl chloride have been explored for their role in enzyme inhibition, particularly in carbonic anhydrase inhibitors and protease inhibitors. The presence of the dimethylsulfamoyl moiety can enhance molecular stability and solubility, making it a valuable modification in drug design.

In agrochemistry, dimethylsulfamoyl chloride is used in the synthesis of herbicides, fungicides, and insecticides. Sulfonamide-containing agrochemicals exhibit selective biological activity, and the incorporation of a dimethylsulfamoyl group can contribute to improved efficacy and environmental stability.

Beyond pharmaceuticals and agrochemicals, dimethylsulfamoyl chloride is employed in materials science for the modification of polymers and surface coatings. Its ability to introduce sulfamoyl functionality into polymeric structures enhances chemical resistance, hydrophilicity, and adhesion properties, making it useful in specialized applications such as biomedical materials and industrial coatings.

Due to its reactive sulfonyl chloride group, dimethylsulfamoyl chloride must be handled with caution. It is moisture-sensitive and hydrolyzes readily in the presence of water, releasing hydrogen chloride (HCl), which can cause irritation to the respiratory system, skin, and eyes. Proper safety measures, including the use of gloves, protective eyewear, and working in a fume hood, are necessary when handling this compound. Storage in an airtight container under an inert atmosphere is recommended to prevent degradation and maintain purity.

The role of dimethylsulfamoyl chloride in chemical synthesis continues to be significant, particularly in the development of new pharmaceuticals and functional materials. Its well-documented reactivity and utility in forming sulfonamide derivatives ensure its continued relevance in both industrial and academic research.

References

2022. N,N-dimethyl fluorosulfonamide for suppressed aluminum corrosion in lithium bis(trifluoromethanesulfonyl)imide-based electrolytes. Nano Research, 15(10).
DOI: 10.1007/s12274-022-4669-8

2018. Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions. Synthesis, 50(22).
DOI: 10.1055/s-0037-1610223