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Description
TCI F0706 4-Fluoro-2-iodoaniline is an aniline compound bearing both a fluorine atom and an iodine atom on its aromatic ring, together with a free amine group. The material belongs to the class of fluorinated building blocks that are highly valued in organic synthesis laboratories, because it provides three distinct points of reactivity within a single, structurally simple molecule. The adjacent arrangement of the amine group and the halogen substituents makes it a classical starting material for constructing fused heterocyclic ring systems, and at the same time a reliable reaction partner in the many transition-metal-catalysed transformations that are widely used today.
The principal property behind its selection is the markedly higher reactivity of the iodine atom compared with other halogens in cross-coupling reactions. The carbon–iodine bond is relatively easy to cleave with palladium or copper catalysts, so reactions such as Sonogashira, Suzuki and Heck coupling can proceed under conditions that are not unduly harsh. The fluorine atom, meanwhile, survives the coupling step intact and remains in the final product as a substituent that influences the electronic character of the molecule. The free amine group can act as an internal nucleophile for a subsequent cyclisation step, or it can be acylated or otherwise derivatised as the synthetic route requires.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis, medicinal chemistry and materials chemistry, where fluorinated intermediates are needed for the preparation of target compounds. It is normally handled at small to moderate scale on the bench, in methodology development work, in postgraduate research projects and in the stepwise assembly of heterocyclic scaffolds, where a single reagent offering several orthogonal handles helps keep a synthetic route short.
Laboratory Applications
Sonogashira coupling: the reactive carbon–iodine bond couples readily with terminal alkynes under palladium and copper catalysis, giving ortho-alkynyl anilines that are direct precursors to indole ring systems.
Suzuki coupling: the iodine position undergoes selective arylation with boronic acids under mild palladium catalysis, allowing biaryl frameworks to be assembled while the fluorine substituent remains untouched.
Heck reaction: the compound serves as the aryl halide partner with alkenes, since the carbon–iodine bond is cleaved efficiently by palladium catalysts without requiring forcing reaction conditions.
Fused heterocycle construction: the neighbouring free amine and iodine allow tandem coupling and cyclisation sequences, letting researchers build fused nitrogen-containing ring systems from one simple starting material.
Fluorinated intermediate preparation: the retained fluorine atom modifies the electronic properties of the final product, which is useful when synthesising fluorine-bearing targets for medicinal and materials chemistry studies.
Specifications
Brand: TCI
CAS number: 61272-76-2
Product code: F0706
Category: Chemistry > Building Blocks > Fluorinated Building Blocks
Pack sizes: available in the catalogue pack sizes offered by TCI for this item
Storage: keep in a closed original container, protected from light and stored under the conditions stated on the manufacturer's label
Handling and Storage
Store the material in its tightly closed original container, in a cool, dry and well-ventilated place away from direct sunlight and heat sources, following the conditions stated on the manufacturer's label and safety data sheet. Iodinated anilines are generally light-sensitive, so amber or otherwise light-protected glass containers are appropriate, and the container should be reclosed promptly after each use. Handle the compound in a fume hood using gloves, safety glasses and a laboratory coat, avoid contact with skin and eyes and avoid inhaling dust or vapour. Keep it separate from strong oxidising agents, and dispose of residues and contaminated materials as chemical waste in accordance with the laboratory's own procedures.
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