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CAS 645-00-1

1-Iodo-3-nitrobenzene TCI I0063

1-Iodo-3-nitrobenzene TCI I0063

Chemical Identity

CAS No.
645-00-1
PubChem
CID 12574·SID 87571467
Formula
C6H4INO2
Molecular weight
249.01 g/mol
Purity
>98.0%(GC)
Reference databases
ChEBI·ChemSpider·ECHA
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
1-iodo-3-nitrobenzene
SMILES
C1=CC(=CC(=C1)I)[N+](=O)[O-]
InChIKey
CBYAZOKPJYBCHE-UHFFFAOYSA-N
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TCI I0063 1-Iodo-3-nitrobenzene is the meta isomer of nitroiodobenzene, an aromatic compound in which an iodine atom and a nitro group are separated by one position on the benzene ring. As a non-heterocyclic building block, it supplies a 1,3-substitution pattern that is often difficult to construct through direct aromatic substitution reactions, so using it saves a considerable number of synthetic steps. Researchers rely on it to insert a meta-substituted aromatic ring into larger molecules, whether in drug compound research, dye chemistry, or specialty functional organic materials.

The most prominent characteristic of this compound is the reactivity of the carbon–iodine bond toward transition metal catalysts, which allows a wide range of cross-coupling reactions to proceed efficiently without requiring high temperatures or unnecessarily complicated ligands. The nitro group in the meta position is a strong electron-withdrawing substituent and influences the distribution of electron density across the ring, making it useful both for directing subsequent reactions and as a group that can later be reduced to an amine. This dual character is precisely what makes the compound valued: a single molecule provides two working points with distinct chemical behaviour.

In Indonesian laboratories, this building block is typically found in university synthetic organic chemistry groups, in research institute laboratories developing new molecules, and in industrial R&D units working on dyes and functional organic materials. It is normally ordered in small research quantities rather than production volumes, since it serves as an intermediate consumed early in a synthetic route. Its role is to shorten the path to a target structure that would otherwise demand several additional preparative steps.

  • Palladium-catalysed cross-coupling reactions, where the reactive carbon–iodine bond allows Suzuki, Sonogashira, and related couplings to proceed efficiently under mild conditions without demanding ligands.
  • Construction of meta-substituted aromatic scaffolds, providing a 1,3-substitution pattern directly instead of forcing chemists through several controlled direct aromatic substitution steps.
  • Medicinal chemistry building block work, where the meta-disubstituted ring is introduced into larger candidate molecules during exploratory drug compound research programmes.
  • Synthesis of dye intermediates, since the aromatic ring carrying both iodine and a nitro group serves as a starting framework for coloured organic structures.
  • Preparation of aromatic amines by reduction, in which the meta nitro group is converted into an amine to give a second, chemically distinct reaction point.

Brand TCI (Tokyo Chemical Industry)
CAS number 645-00-1
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes available in research-scale laboratory packs; please confirm currently listed sizes when ordering
Physical form —
Storage keep in a tightly closed original container, protected from light and stored in a cool place
  • Catalogue code: I0063

Store the container tightly closed in a cool, dry, and well-ventilated area, away from direct sunlight, heat sources, and strong oxidising agents. The original supplier packaging is the most suitable container, as iodinated aromatic compounds are generally sensitive to light; where transfer is necessary, use amber glass or another light-protecting vessel with a chemically compatible closure. All handling, weighing, and transfer operations should be carried out in a fume hood using gloves, safety glasses, and a laboratory coat, since aromatic nitro compounds require care in avoiding skin contact and inhalation of dust or vapour. Keep the container labelled, return it promptly to its designated storage location after use, and consult the manufacturer's safety data sheet before first handling and before waste disposal.

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