4-(Dimethylamino)benzenesulfonamide: Properties & Lab Uses

4-(Dimethylamino)benzenesulfonamide is an aromatic sulfonamide compound featuring a dimethylamino electron-donating group para to the sulfonamide moiety, making it a versatile intermediate and reagent in organic synthesis and pharmaceutical research.

CAS Number

Needs verification — not confirmed in source material

Molecular Formula

C₈H₁₂N₂O₂S

Molecular Weight

200.26 g/mol (calculated)

Functional Groups

Sulfonamide (–SO₂NH₂) and dimethylamino (–N(CH₃)₂)

Compound Class

Aromatic sulfonamide

SKU

B727786

Chemical Structure and Properties

4-(Dimethylamino)benzenesulfonamide belongs to the sulfonamide class of organic compounds. Its structure consists of a benzene ring bearing a dimethylamino group (–N(CH₃)₂) at the para position relative to the sulfonamide group (–SO₂NH₂). The dimethylamino substituent acts as a strong electron-donating group through resonance, significantly influencing the electron density of the aromatic ring and altering the reactivity of the sulfonamide nitrogen.

The compound is a solid at room temperature. The push-pull electronic character between the electron-donating dimethylamino group and the electron-withdrawing sulfonamide group makes this molecule particularly interesting for spectroscopic and reactivity studies. The sulfonamide –NH₂ protons can participate in hydrogen bonding, affecting solubility and crystal packing properties.

Synthesis and Preparation

Aromatic sulfonamides such as 4-(Dimethylamino)benzenesulfonamide are generally accessible via the reaction of the corresponding sulfonyl chloride with ammonia or an ammonium source. The precursor, 4-(dimethylamino)benzenesulfonyl chloride, can be prepared from 4-(dimethylamino)aniline through a diazotization-sulfonation sequence followed by chlorination, or directly through sulfonylation chemistry.

Ammonolysis of the sulfonyl chloride intermediate with concentrated aqueous ammonia or gaseous ammonia under controlled conditions typically affords the primary sulfonamide in good yield. Researchers should handle the sulfonyl chloride precursor with appropriate care, as it is moisture-sensitive and a potential irritant. The final product may be purified by recrystallization from suitable solvents such as ethanol or aqueous ethanol mixtures.

Laboratory Applications

4-(Dimethylamino)benzenesulfonamide serves multiple roles in research settings. As a building block in medicinal chemistry, the electron-rich dimethylamino group and the sulfonamide moiety both offer sites for further functionalization, enabling the construction of more complex drug-like scaffolds. Sulfonamide-containing compounds have a well-established history in pharmaceutical development, including antibacterial agents and carbonic anhydrase inhibitors.

In analytical chemistry, the extended conjugation between the dimethylamino donor and the sulfonamide acceptor may impart useful UV-Vis absorption characteristics, potentially making derivatives of this compound applicable as chromogenic probes or dye intermediates. Additionally, the compound may be used as a reference standard or calibration material in method development for sulfonamide detection assays.

Researchers in agrochemical and materials science fields may also find utility in this compound as an intermediate for the preparation of novel sulfonamide-based ligands or functional materials.

Handling, Storage, and Safety

As with all laboratory chemicals, 4-(Dimethylamino)benzenesulfonamide should be handled in accordance with standard laboratory safety practices. Personnel should wear appropriate personal protective equipment, including gloves, safety glasses, and a laboratory coat. Work should be conducted in a well-ventilated area or fume hood to minimize inhalation exposure.

The compound should be stored in a tightly sealed container in a cool, dry location away from incompatible materials such as strong oxidizers and strong acids. Specific storage temperature and shelf-life data should be confirmed from the product's Safety Data Sheet (SDS) provided by Aladdin Scientific. Disposal must comply with applicable local, national, and institutional regulations for chemical waste.

Note: Detailed hazard classification and GHS pictograms for this specific compound should be verified against the current SDS, as precise toxicological data were not available in the source material provided.

Purity, Specifications, and Ordering

Aladdin Scientific offers 4-(Dimethylamino)benzenesulfonamide under product SKU B727786. Researchers and procurement teams should refer to the current product listing for up-to-date information on available quantities, purity grades, pricing, and lead times.

For research applications requiring high reproducibility, it is advisable to request a Certificate of Analysis (CoA) confirming purity by HPLC or other analytical methods. Lot-specific CoA documents are typically available upon request and are essential for regulatory compliance in GMP-adjacent research environments.

For bulk inquiries, custom packaging, or technical questions about this compound, contact Aladdin Scientific's technical support team directly through the website or customer service channels.

Frequently asked questions

What is 4-(Dimethylamino)benzenesulfonamide used for in research?

4-(Dimethylamino)benzenesulfonamide is primarily used as a synthetic intermediate in medicinal chemistry and organic synthesis. Its combination of an electron-donating dimethylamino group and a sulfonamide moiety makes it a versatile building block for constructing drug-like molecules and functional materials. It may also serve as a reference standard in analytical methods for sulfonamide detection.

How should 4-(Dimethylamino)benzenesulfonamide be stored?

The compound should be stored in a tightly sealed container in a cool, dry location, away from strong oxidizers and strong acids. Researchers should consult the product's Safety Data Sheet (SDS) provided by Aladdin Scientific for specific recommended storage temperatures and shelf-life information, as precise conditions should be verified on a lot-specific basis.

What is the molecular formula and molecular weight of 4-(Dimethylamino)benzenesulfonamide?

4-(Dimethylamino)benzenesulfonamide has the molecular formula C₈H₁₂N₂O₂S and a calculated molecular weight of approximately 200.26 g/mol. These values are derived from its structural composition: a benzene ring, a dimethylamino group, and a sulfonamide group. Researchers should confirm these values against the Certificate of Analysis for the specific lot purchased.

Where can I purchase 4-(Dimethylamino)benzenesulfonamide?

4-(Dimethylamino)benzenesulfonamide is available from Aladdin Scientific under SKU B727786. You can place orders directly through the Aladdin Scientific website or contact the customer service team for bulk orders, pricing, and availability inquiries.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for sulfonamide chemistry.
2. Aladdin Scientific. Product listing for 4-(Dimethylamino)benzenesulfonamide, SKU B727786. Aladdin Scientific website.
3. Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opinion on Therapeutic Patents, 2006. General reference for sulfonamide pharmacology.

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