(Ethyl(methyl)sulfamoyl)amine
[CAS# 154743-05-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: (Ethyl(methyl)sulfamoyl)amine
• Synonyms: [methyl(sulfamoyl)amino]ethane
• Molecular Formula: C₃H₁₀N₂O₂S
• Molecular Weight: 138.19
• CAS Registry Number: 154743-05-2
• EC Number: 818-444-6
• SMILES: CCN(C)S(=O)(=O)N

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 231.4±23.0 °C 760 mmHg (Calc.)^*
• Flash point: 93.7±22.6 °C (Calc.)^*
• Index of refraction: 1.498 (Calc.)^*

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

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
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

(Ethyl(methyl)sulfamoyl)amine is a small organosulfur compound belonging to the class of sulfamides, specifically a disubstituted sulfamoylamine. Its structure features a central sulfur atom double-bonded to two oxygen atoms (a sulfonyl group, –SO₂), and bonded to one ethylamino group (–NHCH₂CH₃) and one methylamino group (–NHCH₃), yielding a molecule formally known as *N-ethyl-N-methylsulfamide*.

The general formula of this compound can be represented as CH₃–NH–SO₂–NH–CH₂CH₃, highlighting the sulfonamide backbone with asymmetrical substitution. This gives the molecule moderate polarity, solubility in polar organic solvents, and potential hydrogen bonding capability through the NH groups.

The synthesis of (ethyl(methyl)sulfamoyl)amine typically involves the controlled reaction of sulfamoyl chloride (ClSO₂NH₂) with a mixture of primary and secondary amines—specifically methylamine and ethylamine. By adjusting stoichiometry and reaction conditions, selective monoalkylation at each nitrogen can be achieved, avoiding symmetrical bis-substitution. Such reactions are generally carried out in aprotic solvents like dichloromethane or acetonitrile in the presence of a base (e.g., triethylamine) to neutralize the generated hydrochloric acid.

Although (ethyl(methyl)sulfamoyl)amine is not widely known as a stand-alone pharmacologically active agent, sulfonamide derivatives in general occupy a well-established niche in medicinal chemistry. They are frequently found in antibacterial drugs (like sulfa drugs), diuretics, antidiabetics, and protease inhibitors. The sulfamide group is notable for its ability to mimic tetrahedral transition states or phosphate esters in enzyme active sites, and to form stable hydrogen bonds—making it a valuable functional group in drug design.

The presence of both N-alkyl groups in (ethyl(methyl)sulfamoyl)amine modulates its electronic and steric profile compared to primary sulfamides. This kind of asymmetry is often used to fine-tune biological activity and metabolic stability in analog development. In organic synthesis, such molecules may serve as linkers, reagents, or fragments for larger combinatorial libraries.

In conclusion, (ethyl(methyl)sulfamoyl)amine is a synthetically accessible sulfamide compound characterized by its disubstituted sulfonamide framework. While not widely studied as an individual therapeutic agent, it exemplifies a class of compounds important in the development of bioactive molecules and continues to be relevant in medicinal and synthetic organic chemistry.