4-tert-Butylbenzenesulfonamide (CAS No. 6292-59-7)

4-tert-Butylbenzenesulfonamide, also known as p-tert-butylbenzenesulfonamide, is a specialized organosulfur compound serving as a critical intermediate in pharmaceutical synthesis. With the chemical formula C₁₀H₁₅NO₂S, it appears as a white to off-white solid that is stable under ambient conditions. This sulfonamide derivative is particularly valued for its role in the production of endothelin receptor antagonists and as a reference standard for impurity profiling, offering reliable performance in analytical and synthetic applications due to its defined structure and solubility profile.

CAS Number: 6292-59-7 Molecular Weight: 213.30 g/mol Synonyms: 4-(1,1-Dimethylethyl)benzenesulfonamide, p-tert-Butylbenzenesulfonamide, 4-(tert-Butyl)benzenesulfonamide

Key Properties

4-tert-Butylbenzenesulfonamide displays consistent physical and chemical attributes that make it suitable for precise laboratory and industrial use. The table below summarizes essential specifications:

Property Value/Description
Appearance White to off-white solid
Purity ≥98.0% (HPLC)
Melting Point 136-138°C
Boiling Point 337°C (predicted)
Density 1.15 g/cm³ (predicted)
Solubility Slightly soluble in chloroform; sparingly soluble in ethyl acetate
pKa 10.22 (predicted)
Storage Conditions Sealed in dry, room temperature

These properties ensure ease of handling and compatibility with standard organic synthesis protocols, minimizing degradation risks.

P-tert-butylbenzenesulfonamide Applications and Uses

4-tert-Butylbenzenesulfonamide’s sulfonamide functionality supports its integration into advanced chemical processes, with primary applications including:

  • Pharmaceutical Intermediates: Key building block and degradation impurity reference for Bosentan, an endothelin receptor antagonist used in treating pulmonary arterial hypertension.
  • Organic Synthesis: Employed in the preparation of sulfonamide derivatives for drug discovery, leveraging its steric bulk from the tert-butyl group for selective reactions.
  • Analytical Chemistry: Utilized as a standard in HPLC and LC-MS methods for impurity detection in pharmaceutical formulations.
  • Proteomics and Research: Serves as a reagent in biochemical studies involving protein modification and enzyme inhibition assays.
  • Fine Chemicals: Contributes to the synthesis of specialty polymers and agrochemical analogs requiring stable sulfonamide linkages.

Its high purity and structural predictability make it indispensable for quality-controlled manufacturing and research endeavors.

Safety and Handling

4-tert-Butylbenzenesulfonamide is classified as an irritant, potentially causing skin, eye, and respiratory irritation upon exposure. It is harmful if swallowed, inhaled, or absorbed through skin. Recommended safety measures include:

  • Storage: Store in a sealed, dry container at room temperature, away from moisture, strong oxidizers, and acids to prevent hydrolysis or contamination.
  • Handling: Wear protective gloves, safety goggles, and a lab coat. Use in a well-ventilated area or fume hood; avoid generating dust and minimize skin/eye contact.
  • Environmental Impact: Low acute toxicity to aquatic life; dispose of as hazardous waste per local regulations to avoid soil or water ingress.
  • Regulatory Compliance: Hazard codes Xi (irritant); aligns with GHS standards (H315, H319) and REACH/TSCA for irritants.

For comprehensive guidance, request the Safety Data Sheet (SDS).

Frequently Asked Questions (FAQs)

What is the main application of 4-tert-Butylbenzenesulfonamide?

It is primarily used as a pharmaceutical intermediate and degradation impurity marker for Bosentan, supporting synthesis and quality control in hypertension drug production.

Is 4-tert-Butylbenzenesulfonamide safe for laboratory handling?

It poses irritation risks to skin, eyes, and respiratory tract, but is manageable with standard PPE and ventilation; not classified as highly toxic or flammable.

What is the shelf life of 4-tert-Butylbenzenesulfonamide?

When stored sealed and dry at room temperature, it remains stable for 2-3 years, with minimal degradation if protected from humidity.

Can 4-tert-Butylbenzenesulfonamide be shipped internationally?

Yes, it is shipped globally in compliance with IATA and DOT regulations, packaged in moisture-proof containers like HDPE bottles or drums for lab to bulk quantities.

How does 4-tert-Butylbenzenesulfonamide compare to unsubstituted benzenesulfonamide?

The tert-butyl substituent provides steric hindrance and lipophilicity, enhancing solubility in organic solvents and selectivity in reactions compared to the parent compound.

Is 4-tert-Butylbenzenesulfonamide soluble in water?

No, it has low water solubility; it dissolves better in polar organic solvents like chloroform or ethanol for reaction and extraction purposes.

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