2-bromo-3-octylthiophene

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Comprehensive Guide to 2-Bromo-3-Octylthiophene

Table of Contents

1. Basic Information & Specifications

2-Bromo-3-octylthiophene (CAS: 134506-44-8) is a brominated thiophene derivative with the molecular formula C12H19BrS and a molecular weight of 275.25 g/mol. Key specifications include:

Parameter Value
Appearance Clear to pale yellow liquid
Purity ≥98% (GC)
Boiling Point ~320°C (at 760 mmHg)
Solubility Soluble in THF, DCM, chloroform; insoluble in water

2. Detailed Applications

This compound is widely used in:

  • Organic Electronics: Building block for conductive polymers (e.g., P3HT derivatives) in OLEDs and organic photovoltaics.
  • Pharmaceuticals: Intermediate in synthesizing kinase inhibitors and anticancer agents.
  • Agrochemicals: Precursor for fungicides and herbicides.
  • Material Science: Monomer for functionalized polymers with tunable optoelectronic properties.

3. Parameter Comparison with Similar Compounds

Compound Reactivity Thermal Stability Cost Efficiency
2-Bromo-3-octylthiophene High (Suzuki coupling) Stable up to 200°C $$$
3-Hexylthiophene Moderate Stable up to 180°C $$
2-Bromo-5-methylthiophene Low Stable up to 150°C $$$

4. Usage Guidelines

  • Store under inert gas (N2 or Ar) at 2-8°C to prevent bromine displacement.
  • Use anhydrous solvents for reactions requiring high selectivity.
  • Optimal polymerization conditions: 60-80°C with Pd(PPh3)4 catalyst.

5. Industry Case Studies

Case 1: High-Efficiency OLED Manufacturing

A leading display company synthesized P3HT-Br using 2-bromo-3-octylthiophene, achieving 18% external quantum efficiency (EQE) in red-emitting OLEDs.

Case 2: Anticancer Drug Intermediate

PharmaCorp utilized this compound to develop a Bruton’s tyrosine kinase (BTK) inhibitor, reducing synthesis steps from 12 to 8 compared to traditional routes.

6. Real Client Use Cases

Client A: Organic Semiconductor Producer

  • Requirement: 500 kg/year for P3HT-based solar cells
  • Result: 12% power conversion efficiency (PCE) in bulk heterojunction devices

Client B: Agrochemical Innovator

  • Application: Synthesis of a broad-spectrum fungicide
  • Outcome: 95% yield in key bromination step, reducing production costs by 20%

7. Request a Quote

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