2-Bromo-4-tert-butylphenol(CAS#2198-66-5)

1. Properties:

• Appearance and Physical Form: 2-Bromo-4-tert-butylphenol is supplied as a white to colorless, yellow, or green powder, lump, or clear liquid at room temperature. It is available in various high-purity grades (≥97.0%–98.0%) for pharmaceutical R&D, agrochemical synthesis, and advanced materials research.
• Solubility: The compound is soluble in methanol and other common organic solvents. Its brominated phenolic structure provides enhanced solubility in organic media compared to chlorinated analogues.
• Chemical Properties: 2-Bromo-4-tert-butylphenol (C₁₀H₁₃BrO) is a brominated hindered phenol featuring a bromine atom at the ortho position and a tert-butyl group at the para position relative to the hydroxyl group. The tert-butyl group provides steric hindrance, while the bromine atom offers a versatile handle for cross-coupling and substitution reactions.
  • Building Block for SERMs: The compound binds to the estrogen receptor without agonist activity, making it a critical scaffold for selective estrogen receptor modulators (SERMs).
  • Polymerization Catalyst Ligand: Enables synthesis of octahedral Group 4 bis(phenolate) ether catalysts yielding polypropylene with mmmm >99.6% and Tm up to 169.9°C.
  • Synthetic Versatility: Used to produce esters, ethers, and polymers. The bromine atom is more electronegative than chlorine, providing more efficient catalytic activity.
  • Antimicrobial and Antioxidant Properties: Research indicates the compound can inhibit the growth of various bacteria and fungi, making it a candidate for developing new antimicrobial agents.

2. Applications:

Pharmaceutical Research & Drug Discovery:

• SERM Development: Serves as a critical scaffold for selective estrogen receptor modulators (SERMs).
• Pharmaceutical Intermediate: Widely used as a synthetic intermediate in the preparation of pharmaceuticals and bioactive molecules.

Polymer & Catalyst Research:

• Polymerization Catalysts: Enables synthesis of single-site polymerization catalysts for high-performance polypropylene with mmmm >99.6%.
• Polymer Additives: Used in the synthesis of specialty chemicals, including antioxidants and polymer additives.

Agrochemical Research:

• Agrochemical Intermediate: Serves as a building block for the development of crop protection agents.

Organic Synthesis:

• Synthetic Intermediate: Used to prepare 2-mesityl-4-tert-butylphenol and other complex molecules.
• Catalyst Precursor: Shown to be an effective catalyst for the production of hydrochloric acid from hydrogen chloride gas.

3. Preparation Method:

• Synthesis: 2-Bromo-4-tert-butylphenol is typically synthesized via the bromination of 4-tert-butylphenol. The process optimization has been achieved through substitution of chlorinated phenolic compounds with brominated analogues, which provides better solubility in organic solvents and more efficient catalytic activity. The compound is commercially available at >97% purity (GC).

4. Safety Information:

• Hazard Classification: 2-Bromo-4-tert-butylphenol is classified as a hazardous substance. Under GHS, it carries the following hazard statements:
  • H302 + H312 + H332 : Harmful if swallowed, in contact with skin, or if inhaled.
  • H315 : Causes skin irritation.
  • H319 : Causes serious eye irritation.
• Hazard pictogram: GHS07.
• Signal word: Warning.
• Flash Point: 40°F (4°C).
• Health Hazards:
  • Inhalation: Harmful if inhaled. Vapors may cause drowsiness and dizziness.
  • Skin Contact: Harmful in contact with skin. Causes skin irritation.
  • Eye Contact: Causes serious eye irritation.
  • Ingestion: Harmful if swallowed.
  • Reproductive Toxicity: Suspected reproductive hazard (Reproductive toxicity, category 2).
• First Aid Measures:
  • Eye Contact: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing. If eye irritation persists, get medical advice/attention.
  • Skin Contact: Wash with plenty of water. Take off contaminated clothing and wash before reuse. Call a POISON CENTER/doctor if you feel unwell.
  • Inhalation: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor if you feel unwell.
  • Ingestion: Rinse mouth. Call a POISON CENTER/doctor if you feel unwell.
• Personal Protective Equipment (PPE):
  • Respiratory protection: Avoid breathing dust/fume/gas/mist/vapours/spray.
  • Eye protection: Wear eye protection/face protection.
  • Skin protection: Wear protective gloves and protective clothing.
  • General hygiene: Do not eat, drink, or smoke when using this product. Wash skin thoroughly after handling. Use only outdoors or in a well-ventilated area.
• Storage & Stability: Store at room temperature in a cool and dark place (recommended <15°C). Keep container tightly closed. For long-term storage, store in a cool, dry place. Under recommended storage conditions, 2-bromo-4-tert-butylphenol has a shelf life of 12 to 24 months from the date of manufacture in sealed original containers.
• Regulatory Compliance: 2-Bromo-4-tert-butylphenol (CAS#2198-66-5) is listed on EINECS (218-602-9), TSCA, DSL, and other regional chemical inventories. This product is for R&D use only and is not intended for medicinal, household, or other uses. Always consult the Safety Data Sheet (SDS) and local regulations for complete safety, environmental, and regulatory information specific to each product grade and application jurisdiction.
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