4-tertbutylthiophenol

[samir gondaliya]

Introduction

4-tert-Butylthiophenol(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:

1. Thiolation Reactions: Starting from 4-tert-butylchlorobenzene or related compounds, substitution reactions introduce the thiol group.

2. 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.