1-Bromo-2-iodobenzene
[CAS# 583-55-1]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1-Bromo-2-iodobenzene
• Synonyms: 2-Bromoiodobenzene
• Molecular Formula: C₆H₄BrI
• Molecular Weight: 282.91
• CAS Registry Number: 583-55-1
• EC Number: 209-508-9
• SMILES: C1=CC=C(C(=C1)Br)I

Properties

• Density: 2.2±0.1 g/cm³, Calc.^*, 2.203 g/mL (Expl.)
• Melting point: 9-10 ºC (Expl.)
• Index of Refraction: 1.655, Calc.^*, 1.661 (Expl.)
• Boiling Point: 249.7±13.0 ºC (760 mmHg), Calc.^*, 264.4-265.7 ºC (Expl.)
• Flash Point: 104.8±19.8 ºC, Calc.^*, 113 ºC (Expl.)

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

Safety Data

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

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
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

1-Bromo-2-iodobenzene is an organohalogen compound, consisting of a benzene ring substituted with both a bromine atom at position 1 and an iodine atom at position 2. It is commonly used as an intermediate in organic synthesis, particularly in the preparation of more complex chemical compounds.

The discovery of 1-bromo-2-iodobenzene can be traced back to early studies on halogenated aromatic compounds, which have been of interest to chemists due to their varied reactivity and utility in synthetic chemistry. The compound is typically synthesized through halogenation reactions, where bromine and iodine are introduced to the aromatic ring using specific reagents, such as N-bromosuccinimide (NBS) for bromination and iodine or iodine sources for iodination.

1-Bromo-2-iodobenzene has been widely used as a precursor in the synthesis of various organic compounds, particularly in the development of pharmaceuticals, agrochemicals, and materials. The presence of both a bromine and an iodine atom on the aromatic ring allows for further functionalization and the introduction of different substituents at specific positions. This makes it an important building block in the preparation of complex molecules, where the halogen atoms serve as sites for nucleophilic substitution or coupling reactions.

The compound has also been used in cross-coupling reactions, such as the Suzuki or Stille coupling, where it participates in the formation of carbon-carbon bonds. In these reactions, the bromine or iodine atoms are replaced by organic groups, creating new compounds with varying properties and functions. The versatility of 1-bromo-2-iodobenzene in such reactions is one of the reasons it is widely utilized in both academic research and industrial applications.

Additionally, 1-bromo-2-iodobenzene has found use in the preparation of labeled compounds for research purposes, including the synthesis of radiolabeled or isotopically labeled compounds. This application is particularly valuable in areas such as medicinal chemistry and environmental chemistry, where the tracking of chemical pathways or the study of drug metabolism is necessary.

In summary, 1-bromo-2-iodobenzene is a valuable intermediate in organic synthesis, with applications spanning the preparation of pharmaceuticals, agrochemicals, and materials. Its utility in cross-coupling reactions and as a building block for further functionalization underscores its importance in modern synthetic chemistry.

References

2018. Photoinduced Cross-Coupling of Amines with 1,2-Diiodobenzene and Its Application in the Synthesis of Carbazoles. Synthesis, 50(11).
DOI: 10.1055/s-0037-1609444

2020. Flow Synthesis of Triptycene via Triple Cycloaddition of Ynolate to Benzyne. Synlett, 31(14).
DOI: 10.1055/s-0040-1706417

2021. Synthesis from 2-(Phenylethynyl)aniline and 1,2-Dihalobenzenes. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-110-01882