Chemical Identity and Structure

3-(tert-Butyl)benzene-1,2-diol (CAS 3538-51-0), commonly referred to as 3-tert-butylcatechol, belongs to the catechol (benzene-1,2-diol) family of phenolic compounds. Its molecular formula is C₁₀H₁₄O₂ with a molecular weight of 166.22 g/mol. The compound features two adjacent hydroxyl groups on the benzene ring at positions 1 and 2, with a sterically bulky tert-butyl group at position 3.

The presence of the tert-butyl substituent increases the lipophilicity of the molecule relative to unsubstituted catechol, improving solubility in non-polar organic solvents while retaining the characteristic hydrogen-bonding capacity and redox activity of the catechol moiety. This balance of properties distinguishes 3-(tert-Butyl)benzene-1,2-diol from simpler catechols and makes it a valuable building block in research chemistry.

Research Applications

3-(tert-Butyl)benzene-1,2-diol is employed across several research domains owing to its dual-hydroxyl functionality and tunable steric and electronic properties:

• Antioxidant Studies: Catechol derivatives are well-established free-radical scavengers. The tert-butyl group modulates the oxidation potential and membrane permeability, making this compound a useful reference standard or test molecule in antioxidant assays.
• Organic Synthesis: The compound serves as a versatile intermediate in the preparation of more complex phenolic natural product analogues, ligands for metal complexation, and functionalized aromatic scaffolds via selective O-alkylation, O-acylation, or further ring functionalization.
• Coordination Chemistry: Catecholate ligands derived from ortho-diols are well known to coordinate transition metals. 3-tert-Butylcatechol can act as a bidentate O,O-donor ligand in the synthesis of metal complexes for catalysis or materials research.
• Polymer and Materials Chemistry: Catechol-functionalized monomers and additives are of interest in bio-inspired adhesive polymer research. The tert-butyl substituent may be exploited to tune solubility and processing properties.

Handling, Storage, and Safety

As with all catechol-containing phenolic compounds, appropriate laboratory precautions should be observed when working with 3-(tert-Butyl)benzene-1,2-diol:

• Personal Protective Equipment: Wear appropriate gloves, eye protection, and a lab coat. Avoid inhalation of dust or aerosols.
• Storage: Store in a cool, dry, well-ventilated location away from strong oxidising agents and direct light. Keep the container tightly sealed to prevent moisture uptake and oxidative discoloration, which is a common degradation pathway for catechol derivatives.
• Stability: Catechol-type diols are susceptible to aerial oxidation, which can result in browning or darkening of the solid over time. Working under inert atmosphere conditions (e.g., nitrogen or argon) is recommended for sensitive applications.
• Disposal: Dispose of waste material in accordance with local institutional and governmental regulations for organic chemical waste.

Always consult the current Safety Data Sheet (SDS) supplied with the product before use.

Ordering Information

3-(tert-Butyl)benzene-1,2-diol is available from Aladdin Scientific under SKU B690762. Researchers should confirm the required purity grade, pack size, and current availability at the time of ordering. For bulk quantities or custom specifications, contact Aladdin Scientific's technical sales team directly.

When placing an order, have the CAS number (3538-51-0) and SKU (B690762) available to ensure correct product identification and to expedite procurement.