1-Bromo-4-iodobenzene
[CAS# 589-87-7]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1-Bromo-4-iodobenzene
• Synonyms: p-Bromoiodobenzene
• Molecular Formula: C₆H₄BrI
• Molecular Weight: 282.91
• CAS Registry Number: 589-87-7
• EC Number: 209-662-7
• SMILES: C1=CC(=CC=C1Br)I

Properties

• Density: 2.2±0.1 g/cm³, Calc.^*
• Melting point: 89-91 °C (Expl.)
• Index of Refraction: 1.655, Calc.^*
• Boiling Point: 244.8±13.0 °C (760 mmHg), Calc.^*, 266.9-269.5 °C (Expl.)
• Flash Point: 101.9±19.8 °C, Calc.^*

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

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

1-Bromo-4-iodobenzene is an organic compound that belongs to the class of halogenated aromatic compounds, specifically a benzene ring substituted with both a bromine atom at the 1-position and an iodine atom at the 4-position. This compound is part of a broader group of functionalized benzene derivatives that have found widespread application in synthetic chemistry due to their reactivity and versatility.

The discovery and synthesis of 1-bromo-4-iodobenzene are rooted in the continued exploration of halogenated aromatic compounds, which have been of interest for many decades due to their use as intermediates in organic synthesis. Halogenation of aromatic compounds, such as benzene, is a common method for introducing halogens, which can significantly influence the compound’s chemical reactivity. The particular combination of bromine and iodine in 1-bromo-4-iodobenzene makes it a particularly useful reagent in various synthetic applications.

The primary applications of 1-bromo-4-iodobenzene lie in the field of organic synthesis. The presence of both a bromine and an iodine atom on the benzene ring makes this compound highly reactive in various chemical reactions, including cross-coupling reactions. One of the most important reactions involving 1-bromo-4-iodobenzene is the Suzuki-Miyaura coupling reaction, a widely used method for the formation of carbon-carbon bonds. In this reaction, 1-bromo-4-iodobenzene reacts with organoboron compounds in the presence of a palladium catalyst to form biaryl compounds. These biaryl compounds are important intermediates in the synthesis of pharmaceuticals, agrochemicals, and materials science applications.

Another important reaction in which 1-bromo-4-iodobenzene is involved is the Heck reaction, where it serves as a substrate for coupling with alkenes to produce substituted alkenes. This reaction is particularly valuable for the formation of complex organic molecules with extended conjugation, making it useful in the synthesis of organic semiconductors and other advanced materials.

The ability of 1-bromo-4-iodobenzene to undergo nucleophilic substitution reactions also makes it a useful intermediate in the synthesis of a variety of functionalized aromatic compounds. For example, it can be used to introduce new functional groups such as amines, alcohols, or thiols at the aromatic ring. This functionalization can then be used to further modify the compound for specific applications, including in the development of materials for optoelectronics or as potential building blocks for drug design.

In addition to its role in synthetic chemistry, 1-bromo-4-iodobenzene has also been used in the preparation of metal-organic frameworks (MOFs) and other coordination compounds. Due to the halogen atoms, particularly iodine, it can form strong coordination bonds with metal centers, which are important for the development of catalysts used in various chemical processes. These processes can include industrial reactions, such as hydrogenation and C–C bond formation, as well as in environmental applications such as pollutant removal.

Furthermore, 1-bromo-4-iodobenzene is useful in the development of molecular sensors. Its halogenated structure allows for specific interactions with metal ions or other analytes, which can be detected using various spectroscopic methods. This property makes it valuable in the design of chemical sensors used in environmental monitoring, biomedical applications, and food safety testing.

In summary, 1-bromo-4-iodobenzene is an important compound in organic synthesis with applications in cross-coupling reactions, nucleophilic substitution, the development of molecular sensors, and the preparation of metal-organic frameworks. Its ability to react in a variety of chemical reactions makes it a versatile intermediate in the synthesis of pharmaceuticals, agrochemicals, and advanced materials. The well-established applications of 1-bromo-4-iodobenzene in both academic and industrial settings highlight its significance in modern synthetic chemistry.

References

2019. Band Gap Modification of TiO2 Nanoparticles by Ascorbic Acid-Stabilized Pd Nanoparticles for Photocatalytic Suzuki-Miyaura and Ullmann Coupling Reactions. Catalysis Letters, 149(6).
DOI: 10.1007/s10562-019-02749-z

2022. Chemoselective borylation of bromoiodoarene in continuous flow: synthesis of bromoarylboronic acids. Journal of Flow Chemistry, 12(4).
DOI: 10.1007/s41981-022-00246-w

2023. Synthesis and Characterization of Fe3O4@SiO2@MgAl-LDH@Au.Pd as an Efficient and Magnetically Recyclable Catalyst for Reduction of 4-Nitrophenol and Suzuki Coupling Reactions. Arabian Journal for Science and Engineering, 48(8).
DOI: 10.1007/s13369-022-07543-5