3,6-Dibromo-9-(4-dodecyloxyphenyl)-9H-carbazole TCI D5343

Chemical Identity

CAS No.: 865163-47-9
PubChem: CID 86071764·SID 354334840
Formula: C30H35Br2NO
Molecular weight: 585.42 g/mol
Purity: >97.0%(HPLC)(N)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 3,6-dibromo-9-(4-dodecoxyphenyl)carbazole
SMILES: CCCCCCCCCCCCOC1=CC=C(C=C1)N2C3=C(C=C(C=C3)Br)C4=C2C=CC(=C4)Br
InChIKey: VWCTWVHXOOAKSE-UHFFFAOYSA-N

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TCI D5343, 3,6-Dibromo-9-(4-dodecyloxyphenyl)-9H-carbazole, is a carbazole monomer carrying two bromine atoms at the 3 and 6 positions and a phenyl group bearing a twelve-carbon dodecyloxy chain on the nitrogen. In the laboratory it serves as a building block for polymer semiconductors, with particular emphasis on solution processability. The unusually long side chain makes it a practical option for researchers who run into conjugated polymers precipitating or aggregating before they can be cast into uniform thin films.

The key characteristic that leads researchers to select this compound is its alkoxy chain length, which exceeds that of octyloxy and heptyl derivatives. The twelve-carbon chain delivers a stronger solubilizing effect, so that high molecular weight polymers can still be dissolved and filtered. That long chain also influences how the polymer chains pack against one another in the solid state, which in turn affects crystallinity, thermal transition temperatures, and film surface texture. Meanwhile, the two bromine atoms sit at the most reactive positions of the carbazole core and continue to provide selective coupling points for cross-coupling polymerization.

In Indonesian laboratories, this monomer is typically used by university and institutional research groups working on organic electronic materials, where the main practical challenge is producing conjugated polymer solutions that stay homogeneous long enough to be deposited. Groups developing polymer films for optoelectronic studies usually order it in small research quantities, since the material is consumed at synthesis scale rather than in routine analysis. It is normally handled alongside standard cross-coupling reagents and anhydrous solvents already present in a synthetic chemistry laboratory.

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Building Blocks for Organic Semiconductor 2026-03-24 · p. 35

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Conjugated polymer synthesis via cross-coupling: the two bromine atoms at the 3 and 6 positions provide selective, well-defined coupling points that let polymer chains grow in a predictable direction along the carbazole core.
Solution-processable semiconductor development: the twelve-carbon dodecyloxy chain raises solubility enough that high molecular weight polymer product remains dissolved and can be filtered rather than crashing out of solution.
Thin film deposition studies: researchers casting uniform films benefit from a monomer whose long side chain keeps the resulting conjugated polymer from aggregating before the coating step is completed.
Solid-state packing and morphology investigations: the extended alkoxy chain changes how neighbouring polymer chains pack together, making this monomer useful for studies correlating side chain length with crystallinity and film surface texture.
Thermal behaviour characterisation of carbazole polymers: because side chain length influences thermal transition temperatures, this building block suits comparative work against shorter octyloxy or heptyl carbazole derivatives.

Brand	TCI (Tokyo Chemical Industry)
CAS number	865163-47-9
Molecular formula	—
Purity	—
Category	Materials Science > Material Building Blocks > Polymer/Macromolecule Semiconductor Building Blocks
Pack sizes	available in research-scale laboratory pack sizes; please confirm the currently listed pack size when ordering
Physical form	—
Storage	store in a cool, dark place in a tightly sealed container

Chemical name: 3,6-Dibromo-9-(4-dodecyloxyphenyl)-9H-carbazole

Store this monomer in a cool, dark place in its original tightly sealed container, kept away from direct sunlight, heat sources, and moisture. Amber glass or the manufacturer's supplied container is suitable, and the cap should be closed firmly after each use to limit exposure to humid air. Handle the material in a fume hood while wearing gloves, safety glasses, and a laboratory coat, and avoid generating dust when weighing. Use clean, dry spatulas to prevent contamination that could interfere with subsequent polymerization. Consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated consumables through your institution's chemical waste stream.

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