4-Iodobiphenyl
[CAS# 1591-31-7]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 4-Iodobiphenyl
• Synonyms: 1-iodo-4-phenylbenzene
• Molecular Formula: C₁₂H₉I
• Molecular Weight: 280.11
• CAS Registry Number: 1591-31-7
• EC Number: 216-469-1
• SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)I

Properties

• Melting point: 110-114 °C

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H302-H318-H400-H410
• Safety Statements: P264-P264+P265-P270-P273-P280-P301+P317-P305+P354+P338-P317-P330-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 3077

Discovery and Applications

4-Iodobiphenyl is a significant chemical compound in organic chemistry, valued for its role in various chemical reactions and applications. This compound consists of two biphenyl rings connected by an iodine atom at the para position, which imparts unique properties to the molecule.

The discovery of 4-iodobiphenyl can be traced back to early studies in organoiodine chemistry, where researchers were exploring the reactivity and applications of iodine-substituted aromatic compounds. Iodine, as a substituent, introduces distinct electronic and steric effects due to its size and electronegativity, which can greatly influence the chemical behavior of the biphenyl system.

4-Iodobiphenyl is primarily used as an intermediate in the synthesis of more complex molecules. Its role as a versatile building block is crucial in the production of pharmaceuticals, agrochemicals, and materials science. One of its prominent applications is in the synthesis of ligands for palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura reaction. In this reaction, 4-iodobiphenyl acts as a key component that couples with other organoboron compounds to form biaryl systems, which are valuable in various chemical and pharmaceutical applications.

In addition to its role in cross-coupling reactions, 4-iodobiphenyl is also utilized in the creation of liquid crystals. Liquid crystals are materials that exhibit properties between those of conventional liquids and solid crystals, making them useful in display technologies. The incorporation of 4-iodobiphenyl into liquid crystal formulations can modify the alignment and properties of the liquid crystals, enhancing their performance in devices such as LCD screens.

The compound's utility extends to organic synthesis, where it is employed in the preparation of functionalized biphenyl derivatives. These derivatives are important in the development of new materials and chemical products. The reactivity of 4-iodobiphenyl, due to the presence of the iodine atom, allows for various transformations that are not possible with other biphenyl derivatives.

In summary, 4-iodobiphenyl is a valuable compound in organic chemistry, recognized for its role in both industrial and research applications. Its ability to participate in cross-coupling reactions and its application in liquid crystal technology highlight its importance in the synthesis of complex molecules and advanced materials.

References

1981. Biodehalogenation and Metabolism of [125I]-4-iodobiphenyl. Journal of Pharmaceutical Sciences, 70(5), 521-526.
DOI: https://pubmed.ncbi.nlm.nih.gov/7241361

2020. Advances in Carbon-Element Bond Construction under Chan-Lam Cross-Coupling Conditions: A Second Decade. Synthesis, 52(24), 3767-3795.
DOI: 10.1055/s-0040-1705971

2022. Copper-mediated etherification via aryl radicals generated from triplet states. Nature Synthesis, 1(5), 393-402.
DOI: 10.1038/s44160-022-00061-0