4-tert-Butylbenzenethiol (also known as p-tert-butylthiophenol) is an organosulfur compound widely used in organic synthesis, polymer stabilization, and as an intermediate in fine chemicals. Belonging to the thiophenol family, it contains a sulfur–hydrogen (–SH) functional group attached to an aromatic ring substituted with a tert-butyl group at the para position. This structural modification significantly influences its reactivity and applications compared to unsubstituted thiophenol.
Chemical Identity
IUPAC Name: 4-(tert-butyl)benzenethiol
Molecular Formula: C10H14S
Molecular Weight: 166.28 g/mol
Appearance: Typically a colorless to pale yellow liquid with a strong odor
Functional Groups: Aromatic ring, thiol group (–SH), tert-butyl substituent
Properties Physical Properties
Boiling Point: ~ 259–261 °C
Melting Point: ~ –8 °C
Solubility: Insoluble in water; soluble in organic solvents such as ethanol, ether, and benzene
Odor: Strong, characteristic thiol odor
Chemical Properties
Thiol groups are nucleophilic and easily undergo oxidation to form disulfides.
The bulky tert-butyl group increases steric hindrance, affecting the reactivity compared to unsubstituted thiophenol.
Stable under normal storage conditions but can oxidize in air.
Synthesis
4-tert-Butylthiophenol can be synthesized by:
Thiolation Reactions: Starting from 4-tert-butylchlorobenzene or related compounds, substitution reactions introduce the thiol group.
Reduction Pathways: Using precursors such as disulfides or sulfonyl derivatives followed by reduction.
Applications 1. Polymer Stabilization
Used as an antioxidant and chain transfer agent in polymerization processes.
Helps prevent degradation of plastics and rubber by scavenging free radicals.
2. Chemical Intermediate
Serves as a building block in pharmaceuticals, agrochemicals, and specialty chemicals.
Useful in preparing sulfur-containing ligands and catalysts.
3. Research Applications
Employed in organic chemistry laboratories to study thiol-based reactivity.
Acts as a precursor for the synthesis of substituted aromatic sulfur compounds.
Safety and Handling
Hazards: Strong odor, may cause skin and eye irritation, harmful if inhaled.
Precautions: Handle under a fume hood, use gloves and eye protection.
Storage: Store in tightly sealed containers, away from oxidizing agents and moisture.
Conclusion
4-tert-Butylthiophenol is a versatile organosulfur compound valued in polymer stabilization, chemical synthesis, and materials research. Its thiol functionality combined with the steric effects of the tert-butyl group provides unique chemical properties. However, due to its strong odor and potential health hazards, careful handling and proper storage are essential.
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