TCI
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Description
TCI F0815 1-Fluoro-3-iodo-5-nitrobenzene is a trifunctional aromatic building block that places three different substituents symmetrically at the 1, 3, and 5 positions of a benzene ring. Each group carries a distinct chemical role: the iodine atom serves as a point for transition-metal-catalysed cross-coupling, the nitro group acts as an amine precursor and simultaneously activates the ring toward nucleophilic aromatic substitution, and the fluorine atom functions either as a potential leaving group in those reactions or as a permanent substituent that modulates the properties of the final molecule. This structure is highly valued by synthetic chemists because it allows complex molecules to be assembled in a stepwise, controlled manner from a single starting material.
The advantage that leads researchers to select this compound is the possibility of orthogonal functionalisation. Work can begin with a Suzuki, Sonogashira, or Buchwald–Hartwig coupling at the iodo position, because the carbon–iodine bond is far more reactive toward oxidative addition than the carbon–fluorine bond. The nitro group can then be reduced to an aniline, opening routes to amidation or heterocycle formation, or it can be retained to activate nucleophilic substitution at the fluorine position. The symmetric 1,3,5 substitution pattern keeps the reactive sites electronically distinguishable, so each transformation can be directed to one site at a time without protecting-group strategies.
In Indonesian laboratories, a reagent of this type is typically used in university and institutional research groups working on medicinal chemistry, materials chemistry, and methodology development, as well as in industrial R&D units preparing intermediates for further evaluation. It is usually ordered in small research quantities for multi-step synthesis campaigns, where a single versatile scaffold reduces the number of separate starting materials that must be imported and stocked. Laboratories running method development on cross-coupling chemistry also use it as a well-behaved model substrate.
Laboratory Applications
- Suzuki–Miyaura cross-coupling: the reactive carbon–iodine bond undergoes oxidative addition readily, allowing selective introduction of aryl or heteroaryl groups while the fluorine substituent remains untouched.
- Sonogashira coupling: the iodo position accepts terminal alkynes under palladium–copper catalysis, giving access to rigid conjugated arms useful for materials and probe molecules built on a nitroaromatic core.
- Buchwald–Hartwig amination: the iodo site couples with primary or secondary amines, letting chemists install nitrogen substituents before or after manipulating the nitro and fluoro groups elsewhere on the ring.
- Nucleophilic aromatic substitution: the electron-withdrawing nitro group activates the ring so that the fluorine atom can be displaced by oxygen, nitrogen, or sulfur nucleophiles under controlled conditions.
- Aniline intermediate preparation: reduction of the nitro group yields a substituted aniline that serves as a handle for amidation, diazotisation, or heterocycle construction in multi-step medicinal chemistry routes.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS number: 3819-88-3
- Chemical name: 1-Fluoro-3-iodo-5-nitrobenzene
- Category: Chemistry > Building Blocks > Fluorinated Building Blocks
- Pack sizes: supplied in research-scale catalogue pack sizes; please confirm the currently available packaging when ordering
- Storage: keep in the original tightly closed container in a cool, dark place as indicated on the manufacturer's label
Handling and Storage
Store the container tightly closed in a cool, dry, and well-ventilated place away from direct sunlight and heat sources, following the storage condition printed on the manufacturer's label. Keep the material in its original supplier container, or in a chemically compatible amber glass bottle with a well-sealed cap if subdivision is necessary, and label every transferred portion clearly. Handle only in a functioning fume hood while wearing safety goggles, a laboratory coat, and chemically resistant gloves, since nitroaromatic and halogenated aromatic compounds should not be inhaled or allowed to contact skin. Keep the compound separated from strong reducing agents, strong bases, and sources of ignition. Consult the manufacturer's Safety Data Sheet before use and dispose of residues and contaminated materials through the laboratory's designated chemical waste stream.
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