4-Bromotriphenylamine
[CAS# 36809-26-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Imide
• Name: 4-Bromotriphenylamine
• Synonyms: 4-Bromo-N,N-diphenylaniline
• Molecular Formula: C₁₈H₁₄BrN
• Molecular Weight: 324.21
• CAS Registry Number: 36809-26-4
• EC Number: 628-532-4
• SMILES: C1=CC=C(C=C1)N(C2=CC=CC=C2)C3=CC=C(C=C3)Br

Properties

• Melting point: 108-112 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H317-H319-H335-H413
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

4-Bromotriphenylamine is a chemical compound featuring a triphenylamine core structure with a bromine atom substituted at the para position on one of the phenyl rings. This structural modification imparts unique chemical properties, making the compound valuable in various applications, particularly in the fields of organic electronics and materials science.

The discovery of 4-bromotriphenylamine can be traced back to the broader study of triphenylamine derivatives, which have been extensively explored due to their interesting electronic properties. Triphenylamine itself is a well-known electron-donating compound, widely used in organic synthesis and as a building block in the design of organic electronic materials. The introduction of a bromine atom into the triphenylamine structure enhances its reactivity, particularly in reactions that involve the formation of carbon-carbon and carbon-heteroatom bonds, such as palladium-catalyzed cross-coupling reactions.

One of the primary applications of 4-bromotriphenylamine is in the field of organic electronics, where it is used as a precursor in the synthesis of various organic semiconductors and light-emitting materials. The bromine atom in the molecule serves as a reactive site that can be used to introduce additional functional groups, enabling the fine-tuning of the electronic properties of the resulting materials. These materials are crucial components in the development of organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and other organic electronic devices. The triphenylamine core structure provides a stable and efficient platform for charge transport, while the bromine substitution allows for further chemical modification to optimize performance.

In addition to its role in organic electronics, 4-bromotriphenylamine is also utilized in the synthesis of complex organic molecules, including dyes, pigments, and pharmaceuticals. The compound's bromine atom facilitates its participation in various coupling reactions, allowing for the construction of intricate molecular architectures. These reactions are essential in the development of new materials and chemical entities with specific properties and functions. For instance, in the field of medicinal chemistry, triphenylamine derivatives have been investigated for their potential biological activities, including as inhibitors of certain enzymes and receptors.

The versatility of 4-bromotriphenylamine is further demonstrated by its use in the development of advanced materials with tailored electronic properties. Researchers have explored its incorporation into polymers and other macromolecular systems to create materials that exhibit unique optical and electronic behaviors. These materials are of particular interest in the design of sensors, light-harvesting systems, and other functional devices that require precise control over electronic interactions.

Moreover, 4-bromotriphenylamine has been studied for its potential use in organic synthesis as a building block for the preparation of more complex molecules. Its reactivity and stability make it a valuable intermediate in the production of other functionalized triphenylamine derivatives, which are used in a variety of applications, including as catalysts, ligands, and molecular probes. The ability to easily modify the bromine-substituted phenyl ring allows chemists to explore a wide range of chemical transformations, expanding the scope of possible applications.

The continued research into 4-bromotriphenylamine highlights its importance in both academic and industrial chemistry. Advances in synthetic methodologies have allowed for the efficient and selective production of this compound, facilitating its use in various cutting-edge technologies. As the demand for new materials with enhanced electronic properties grows, 4-bromotriphenylamine is likely to remain a key compound in the development of next-generation organic electronic devices and materials.

References

2018. Triphenylamine Derivatives in OLEDs. Journal of Materials Chemistry C, 6(25).
DOI: 10.1039/C8TC01567A