2-Amino-N-Ethylbenzenesulfonamide: Properties & Lab Guide

2-Amino-n-ethylbenzenesulfonamide is a bifunctional aromatic sulfonamide reagent bearing both a free primary amine and a secondary sulfonamide group, making it a versatile building block in medicinal chemistry and organic synthesis.

Chemical Name

2-Amino-N-ethylbenzenesulfonamide

SKU

A188935

Functional Groups

Primary aromatic amine (–NH₂) and secondary sulfonamide (–SO₂NHCH₂CH₃)

Molecular Formula

C₈H₁₂N₂O₂S

Molecular Weight

200.26 g/mol

Appearance

Typically a solid powder at room temperature

Storage Condition

Store in a cool, dry, well-ventilated area away from light and moisture

Chemical Structure and Properties

2-Amino-N-ethylbenzenesulfonamide (SKU: A188935) is an ortho-substituted benzenesulfonamide derivative with the molecular formula C₈H₁₂N₂O₂S and a molecular weight of approximately 200.26 g/mol. The compound features two key nitrogen-containing functional groups on the benzene ring system: a primary aromatic amino group (–NH₂) positioned ortho to the sulfonyl moiety, and a secondary sulfonamide group (–SO₂NHCH₂CH₃) bearing an N-ethyl substituent.

The coexistence of the free amine and the sulfonamide group within the same molecule confers significant synthetic versatility. The aromatic amine is susceptible to acylation, diazotization, and condensation reactions, while the sulfonamide nitrogen can act as a nucleophile or hydrogen-bond donor/acceptor in supramolecular and biological contexts. The compound is expected to be a solid at ambient temperature, with moderate polarity reflecting the balance between its aromatic core and polar functional groups.

Research and Synthetic Applications

2-Amino-N-ethylbenzenesulfonamide serves as a useful bifunctional building block in several areas of chemical research:

• Medicinal Chemistry: Sulfonamide-containing compounds constitute an important class of pharmaceutically active molecules. The free aromatic amine in 2-Amino-N-ethylbenzenesulfonamide can be exploited for further derivatization to generate sulfonamide libraries relevant to drug discovery programs targeting enzymes such as carbonic anhydrases or other sulfonamide-sensitive targets.
• Heterocyclic Synthesis: The ortho-amino sulfonamide scaffold is a classical precursor for the construction of benzothiadiazine, benzothiazole, and related heterocyclic ring systems via intramolecular cyclization or condensation with electrophilic partners.
• Ligand Design: The compound's dual hydrogen-bond donor capability makes it attractive for the design of chelating or coordinating ligands in coordination chemistry and catalysis.
• Biochemical Probes: Ortho-aminosulfonamides have been investigated as scaffolds for enzyme inhibitor design, particularly targeting metalloenzymes where the sulfonamide anion coordinates to active-site metal ions.

Researchers should confirm the specific purity grade and suitability of A188935 for their intended application prior to use.

Safe Handling, Storage, and Disposal

Personal Protective Equipment (PPE): When handling 2-Amino-N-ethylbenzenesulfonamide, wear appropriate PPE including chemical-resistant gloves (nitrile recommended), a laboratory coat, and safety goggles. Where dust generation is possible, use a NIOSH-approved dust mask or work within a fume hood.

Storage: Store the compound in a tightly sealed container in a cool (typically 2–8 °C or room temperature as specified on the product label), dry, and well-ventilated area, protected from light and moisture. Keep away from incompatible materials such as strong oxidizing agents and strong acids.

Handling Precautions: Avoid inhalation of dust or vapors, skin contact, and ingestion. Aromatic amine-containing compounds warrant careful handling due to the potential sensitization or toxicity associated with this chemical class; always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

Disposal: Dispose of this compound and contaminated materials in accordance with local, regional, and national regulations governing chemical waste. Do not dispose of via drain or municipal waste streams without proper authorization.

Emergency Measures: In the event of skin or eye contact, flush immediately with copious amounts of water for at least 15 minutes and seek medical attention. Refer to the SDS for full emergency response procedures.

Quality, Purity, and Procurement Guidance

When procuring 2-Amino-N-ethylbenzenesulfonamide (A188935) from Aladdin Scientific, researchers and lab managers should consider the following:

• Purity Grade: Confirm the stated purity percentage on the Certificate of Analysis (CoA) before use. For sensitive synthetic or biological assay applications, high-purity grades (≥97% or as specified) are recommended to minimize interference from impurities.
• Analytical Characterization: Typical quality control methods for this class of compound include HPLC, NMR spectroscopy (¹H and ¹³C), and mass spectrometry. Request the CoA to verify that the batch meets specification.
• Lot-to-Lot Consistency: For longitudinal studies or scale-up processes, specify the lot number when reordering to facilitate consistency checks.
• Quantity and Packaging: Select appropriate pack sizes based on projected consumption to minimize repeated freeze-thaw cycles or prolonged exposure of the bulk material to ambient conditions.
• Regulatory and Compliance Considerations: Check whether any import/export restrictions or controlled-substance regulations apply in your jurisdiction before ordering.

Contact Aladdin Scientific's technical support team for custom quantities, bulk pricing, or additional analytical data requirements.

Frequently asked questions

What is the molecular formula and molecular weight of 2-Amino-N-ethylbenzenesulfonamide?

2-Amino-N-ethylbenzenesulfonamide has the molecular formula C₈H₁₂N₂O₂S and a molecular weight of approximately 200.26 g/mol. These values should be confirmed against the Certificate of Analysis (CoA) provided with each lot.

What are the primary synthetic applications of 2-Amino-N-ethylbenzenesulfonamide?

This compound is primarily used as a bifunctional building block in medicinal chemistry, heterocyclic synthesis, and ligand design. The ortho-amino group enables acylation, diazotization, and cyclization reactions, while the sulfonamide moiety can serve as a pharmacophore or coordinating group in enzyme inhibitor and coordination chemistry research.

How should 2-Amino-N-ethylbenzenesulfonamide be stored to maintain stability?

The compound should be stored in a tightly sealed container under cool, dry, and well-ventilated conditions, protected from light and moisture. Refer to the product label and SDS for the specific recommended temperature range, as storage requirements may vary by formulation or purity grade.

Is a Safety Data Sheet (SDS) available for A188935?

Yes, Aladdin Scientific provides a Safety Data Sheet for 2-Amino-N-ethylbenzenesulfonamide (A188935). Researchers should obtain and review the current SDS before handling the compound to understand hazard classifications, first-aid measures, and proper disposal procedures.

Can the purity of each batch of A188935 be verified?

Yes, each lot of A188935 is accompanied by a Certificate of Analysis (CoA) detailing the purity and analytical results. Customers may request CoA documentation from Aladdin Scientific at the time of purchase or via the technical support team.

References

1. Patrick, G. L. An Introduction to Medicinal Chemistry, 6th ed.; Oxford University Press: Oxford, 2017. (General reference for sulfonamide pharmacology and synthetic utility.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Reference for aromatic amine and sulfonamide reaction chemistry.)
3. Supuran, C. T. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nature Reviews Drug Discovery 2008, 7, 168–181. doi:10.1038/nrd2467

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.