4-(2-Aminoethyl)benzenesulfonamide
[CAS# 35303-76-5]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 4-(2-Aminoethyl)benzenesulfonamide
• Molecular Formula: C₈H₁₂N₂O₂S
• Molecular Weight: 200.25
• CAS Registry Number: 35303-76-5
• EC Number: 252-501-0
• SMILES: C1=CC(=CC=C1CCN)S(=O)(=O)N

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 145-150 °C (Expl.)
• Index of Refraction: 1.587, Calc.^*
• Boiling Point: 387.4±44.0 °C (760 mmHg), Calc.^*
• Flash Point: 188.1±28.4 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314-H315-H319-H335
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P319-P321-P330-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Skin corrosion	Skin Corr.	1C	H314

Discovery and Applications

4-(2-Aminoethyl)benzenesulfonamide is an organic compound consisting of a benzenesulfonamide group substituted with an aminoethyl side chain at the para position. This compound is characterized by its simple structure, comprising a benzene ring attached to a sulfonamide group (–SO2NH2) and a –CH2CH2NH2 (aminoethyl) group. It is typically synthesized by reacting 4-bromobenzenesulfonamide with ethylenediamine or similar reagents under appropriate conditions to form the desired product.

The discovery of 4-(2-aminoethyl)benzenesulfonamide can be traced back to the mid-20th century, when researchers began to investigate sulfonamide derivatives for their potential pharmacological activities. Sulfonamides themselves had long been recognized for their antibacterial properties, and the addition of aminoethyl side chains to the molecule was expected to enhance the compound’s solubility and reactivity, expanding its range of possible applications.

4-(2-Aminoethyl)benzenesulfonamide has found applications in a variety of fields, including medicinal chemistry, agrochemicals, and industrial processes. In medicinal chemistry, it has been used as a starting material for the synthesis of other biologically active compounds. The aminoethyl group can serve as a site for further functionalization, allowing the synthesis of more complex molecules with diverse activities. For example, it has been utilized in the development of compounds that can selectively target enzymes or receptors, playing a role in anti-inflammatory or anticancer therapies.

One of the key applications of 4-(2-aminoethyl)benzenesulfonamide is in the development of enzyme inhibitors. The sulfonamide group, a common motif in many pharmaceutical agents, acts as a structural feature that can interact with the active sites of enzymes, often leading to inhibition of their activity. The aminoethyl side chain may enhance the binding affinity and specificity of the molecule for certain targets, making it a valuable building block for drug discovery. Additionally, it has been investigated in the context of neurodegenerative diseases, where such compounds may help modulate neurotransmitter systems or interfere with disease progression.

In the agrochemical industry, derivatives of 4-(2-aminoethyl)benzenesulfonamide have been used in the development of herbicides and pesticides. The compound’s sulfonamide structure contributes to its potential for binding to plant enzymes, while the aminoethyl group enhances its absorption and activity in plant tissues. These properties make it an interesting candidate for further research and application in agricultural settings.

Moreover, 4-(2-aminoethyl)benzenesulfonamide is also employed in various synthetic organic reactions. It is used as an intermediate in the production of more complex molecules, often involving reactions with other electrophilic reagents. Its relatively simple structure makes it a versatile reagent in organic synthesis, allowing for the creation of a wide array of functionalized molecules.

References

2019. Sulfonamide Derivatives in Medicinal Chemistry. Bioorganic & Medicinal Chemistry, 27(12).
DOI: 10.1016/j.bmc.2019.03.045