2-Bromo-2',4',6'-triisopropyl-3,6-dimethoxy-1,1'-biphenyl
[CAS# 1402393-56-9]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: 2-Bromo-2',4',6'-triisopropyl-3,6-dimethoxy-1,1'-biphenyl
• Molecular Formula: C₂₃H₃₁BrO₂
• Molecular Weight: 419.40
• CAS Registry Number: 1402393-56-9
• SMILES: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2Br)OC)OC)C(C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.532, Calc.^*
• Boiling Point: 425.7±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 134.5±24.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

2-Bromo-2',4',6'-triisopropyl-3,6-dimethoxy-1,1'-biphenyl, a member of the biphenyl family, is an important compound in organic chemistry and materials science. Its unique structure, characterized by the presence of bromine, isopropyl groups, and methoxy substituents on the biphenyl core, imparts distinct chemical and physical properties that are utilized in various applications.

The discovery of 2-Bromo-2',4',6'-triisopropyl-3,6-dimethoxy-1,1'-biphenyl can be attributed to the need for functionalized biphenyl derivatives with enhanced stability and reactivity. The compound's synthesis typically involves bromination of a triisopropyl- and dimethoxy-substituted biphenyl precursor. This process introduces a bromine atom at the 2-position, which plays a crucial role in further chemical transformations.

One of the primary applications of 2-Bromo-2',4',6'-triisopropyl-3,6-dimethoxy-1,1'-biphenyl is as a versatile building block in organic synthesis. The bromine atom serves as a reactive site for cross-coupling reactions, such as Suzuki-Miyaura and Stille couplings, which are essential for forming complex organic molecules. The compound's triisopropyl groups and methoxy substituents provide steric and electronic effects that influence the reactivity and selectivity of these reactions.

In addition to its role in organic synthesis, 2-Bromo-2',4',6'-triisopropyl-3,6-dimethoxy-1,1'-biphenyl is used in the development of advanced materials. Its structure allows it to participate in the formation of polymers and functional materials with tailored properties. For instance, the compound can be used to create conjugated systems with enhanced electronic and optical characteristics, which are valuable in the production of organic semiconductors and light-emitting devices.

The compound's electronic properties are also significant in the realm of organic electronics. The bromine substitution and the presence of isopropyl and methoxy groups impact the electronic distribution within the biphenyl system, which can be exploited to design materials with specific electronic properties. This makes it suitable for applications in organic photovoltaic cells and field-effect transistors.

Moreover, 2-Bromo-2',4',6'-triisopropyl-3,6-dimethoxy-1,1'-biphenyl's chemical stability and functional groups make it a valuable intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its ability to undergo further functionalization allows chemists to create diverse chemical entities with potential biological activity.

In summary, 2-Bromo-2',4',6'-triisopropyl-3,6-dimethoxy-1,1'-biphenyl is a crucial compound in organic chemistry with applications spanning from synthetic chemistry to materials science. Its unique structure and reactivity provide valuable opportunities for the development of advanced materials and chemical products.

References

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