3819-88-3 | 1-FLUORO-3-IODO-5-NITROBENZENE

CAS:3819-88-3 | 1-FLUORO-3-IODO-5-NITROBENZENE,Description

1-Fluoro-3-iodo-5-nitrobenzene is a halogenated nitrobenzene derivative, a class of compounds known for their diverse applications in organic synthesis and material science. While the specific compound is not directly studied in the provided papers, related compounds with similar substitution patterns on the benzene ring have been investigated for their reactivity and utility in various chemical syntheses.

Synthesis Analysis

The synthesis of halogenated nitrobenzenes typically involves the introduction of halogen and nitro groups into the benzene ring. For example, 1-Fluoro-2,5-dimethoxy-4-nitrobenzene was synthesized with a high yield by nitration of 2-fluoro-1,4-dimethoxybenzene with nitric acid, demonstrating the feasibility of introducing nitro groups into halogenated benzene derivatives. Similarly, the preparation of 2-Fluoro-5-nitrobenzonitrile involved the replacement of a nitro group with a cyano group, indicating the potential for functional group interconversion in halogenated nitrobenzenes.

Molecular Structure Analysis

The molecular structure of halogenated nitrobenzenes is characterized by the presence of electron-withdrawing groups, which can influence the electronic properties of the molecule. For instance, the crystal and molecular structure of 1-(N-fluoro-N-t-butyl)amino-2,4,6-trinitrobenzene revealed a pseudo-tetrahedral coordination for the nitrogen atom and a deformation of the aromatic ring. These structural features can affect the reactivity and interaction of the molecule with other chemical species.

Chemical Reactions Analysis

Halogenated nitrobenzenes undergo various chemical reactions, including electrophilic aromatic substitution and nucleophilic aromatic substitution (SNAr). For example, 1-fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate was used for the quantitative fluorination of aromatic substrates, indicating the potential for electrophilic aromatic substitution reactions. Additionally, the SNAr reactions of 3,4-dihalogenonitrobenzenes with nucleophiles demonstrated the influence of the nitro group on the reactivity of the halogen atoms.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated nitrobenzenes are influenced by the substituents on the benzene ring. The presence of fluorine atoms can lead to the formation of C–H⋯F–C hydrogen bonding, as observed in the crystal structure of 1,2,3,5-tetrafluorobenzene. Moreover, the introduction of electron-withdrawing groups like nitro and halogen atoms can affect the acidity, basicity, and overall stability of the molecule.

Scientific Research Applications

1-Fluoro-3-iodo-5-nitrobenzene is a chemical compound with the molecular formula C6H3FINO2. It is a solid at 20°C and should be stored under inert gas. It is air sensitive and has a melting point between 77.0 to 81.0 °C. It is soluble in methanol.

• 1-Iodo-3-nitrobenzene was used in the synthesis of 5-substituted pyrrolo [3,2- b ]pyridine amide and 3′-nitro-4-methylthiobiphenyl. It was also used in palladium (0) catalyzed cross-coupling reaction between heteroarylzinc iodide and unsaturated iodide.
• 1-Fluoro-3-nitrobenzene was used as an internal standard in the regiospecific silver-mediated fluorination of aryl silanes.
• 1-Iodo-3-nitrobenzene was used in the synthesis of 5-substituted pyrrolo [3,2- b ]pyridine amide and 3′-nitro-4-methylthiobiphenyl. It was also used in palladium (0) catalyzed cross-coupling reaction between heteroarylzinc iodide and unsaturated iodide.
• 1-Fluoro-3-nitrobenzene was used as an internal standard in the regiospecific silver-mediated fluorination of aryl silanes.

Safety And Hazards

1-Fluoro-3-iodo-5-nitrobenzene may cause skin irritation, serious eye irritation, and respiratory irritation. It is recommended to avoid breathing dust/fume/gas/mist/vapors/spray and to use personal protective equipment when handling this compound.

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