• 2,7-Dibromo-9-fluorenone (CAS 14348-75-5) - TCI D3557 - AMI Scientific
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TCI

CAS 14348-75-5

2,7-Dibromo-9-fluorenone TCI D3557

2,7-Dibromo-9-fluorenone TCI D3557
Rp 1.417.500,00
Rp 1.417.500,00
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TCI D3557 2,7-Dibromo-9-fluorenone is a polycyclic aromatic intermediate that serves as a backbone material in a great deal of organic electronics research. The molecule consists of a fluorenone core carrying two bromine atoms at the 2 and 7 positions together with a single ketone group at position 9. This symmetrical arrangement provides two equivalent attachment points for cross-coupling reactions, along with one reactive carbonyl centre in the middle of the structure. For this reason, the compound is frequently used as the starting core in the construction of conjugated polymers, light-emitting oligomers, and organic ligands built on rigid frameworks.

The properties that make this compound a preferred choice are the planar rigidity of the fluorenone core and the electron-withdrawing capability of its carbonyl group. This combination produces an effective electron-acceptor unit in the design of donor–acceptor systems, so that the energy gap and absorption characteristics of the final material can be tuned. Its two aryl bromine atoms are highly responsive to Suzuki, Stille, and Sonogashira reactions as well as Yamamoto polymerisation, allowing conjugation to be extended in a controlled manner. The ketone group at position 9 can also be attacked by organolithium or Grignard nucleophiles to form 9,9-disubstituted derivatives that improve solubility and prevent chain aggregation.

In Indonesian laboratories, this building block is typically found in university and institutional research groups working on organic semiconductors, materials chemistry, and synthetic methodology. It is commonly handled at bench scale for the preparation of monomers and small libraries of derivatives, usually under inert-atmosphere technique in a fume hood. Researchers preparing publications, theses, or collaborative materials-science projects rely on a defined-quality reagent of this type so that coupling results remain reproducible between batches and between laboratories.

  • Suzuki cross-coupling monomer synthesis: the two equivalent aryl bromide sites react cleanly with boronic acids, giving symmetrical extended aromatic products that are ideal for building conjugated backbones.
  • Yamamoto and Stille polymerisation: the symmetrical dibromide functions as a difunctional monomer, allowing controlled chain growth into conjugated polymers with a repeating fluorenone acceptor unit along the main chain.
  • Donor–acceptor system design: the electron-withdrawing carbonyl group at position 9 acts as an acceptor moiety, letting researchers tune the energy gap and absorption profile of the target material.
  • Sonogashira alkynylation chemistry: both bromine positions couple with terminal alkynes to introduce rigid acetylenic linkers, extending conjugation length in light-emitting oligomers and related structures.
  • 9,9-Disubstituted derivative preparation: the reactive ketone centre is readily attacked by organolithium or Grignard reagents, producing substituted derivatives with improved solubility and reduced chain aggregation.

Brand TCI (Tokyo Chemical Industry)
CAS number 14348-75-5
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes available in standard TCI research-scale packaging; please confirm the currently offered pack size when ordering
Physical form —
Storage keep the container tightly closed in a cool, dry, well-ventilated place away from light
  • Chemical name: 2,7-Dibromo-9-fluorenone

Store the container tightly closed in a cool, dry and well-ventilated area, protected from direct sunlight and away from strong oxidising agents, strong bases and sources of ignition. Keep the material in its original amber or opaque supplier container, or transfer it to a clean, dry, chemically compatible glass vessel with a secure closure; label all secondary containers clearly. Handle the solid in a fume hood to avoid generating or inhaling dust, and wear safety glasses, nitrile gloves and a laboratory coat throughout weighing and transfer operations. Because the compound is moisture- and air-sensitive in subsequent coupling steps, allow sealed containers to warm to room temperature before opening to prevent condensation, and reseal promptly after use. Consult the manufacturer's safety data sheet before first use, and dispose of residues and contaminated consumables as halogenated organic chemical waste in line with institutional procedures.

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