3,6-Dibromo-9-(m-tolyl)-9H-carbazole TCI D5424

Chemical Identity

CAS No.: 890653-54-0
PubChem: CID 67328754·SID 468591346
Formula: C19H13Br2N
Molecular weight: 415.13 g/mol
Purity: >98.0%(N)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 3,6-dibromo-9-(3-methylphenyl)carbazole
SMILES: CC1=CC(=CC=C1)N2C3=C(C=C(C=C3)Br)C4=C2C=CC(=C4)Br
InChIKey: VTQPTRCVROSIOM-UHFFFAOYSA-N

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TCI D5424, also known as 3,6-Dibromo-9-(m-tolyl)-9H-carbazole, is a carbazole derivative bearing two bromine atoms at the 3 and 6 positions together with a meta-tolyl group attached to its nitrogen atom. The compound belongs to the class of building blocks used for polymeric and macromolecular semiconductor materials. Having it available in the laboratory helps shorten synthetic routes, because researchers obtain a carbazole framework already functionalised at exactly the right positions, without needing to work through separate bromination and N-arylation steps that each require their own purification and risk lowering the overall yield.

The characteristic that makes this material a frequent choice is the simplicity of its substituents. The meta-tolyl group carries only a single methyl group, so the molecular weight stays light, yet it is already sufficient to improve solubility and to slightly disrupt overly ordered intermolecular stacking. The meta position keeps the methyl group away from the N-aryl bond, so steric hindrance around the nitrogen remains moderate. The two bromine atoms at the 3 and 6 positions provide equivalent reaction points for Suzuki coupling, Stille coupling, and Yamamoto polymerisation, giving researchers freedom in designing the polymers they target.

In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic electronic materials, where synthetic capacity is available but time and reagent budgets are limited. Starting from a pre-functionalised carbazole core lets a research team move directly to the coupling or polymerisation step that actually defines their target structure, which suits graduate-level project timelines and reduces the number of intermediate purifications that a shared laboratory has to accommodate.

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Building Blocks for Organic Semiconductor 2026-03-24 · p. 21

Related TCI products

Suzuki cross-coupling polymerisation: the two equivalent bromine atoms at the 3 and 6 positions react cleanly with boronic acid or boronate partners, allowing controlled construction of conjugated backbones.
Stille coupling for conjugated systems: the dibromo pattern serves as a reliable electrophilic partner with organotin reagents, giving researchers a second route when boronate chemistry is unsuitable.
Yamamoto polymerisation: the symmetric placement of both bromine atoms permits direct homocoupling into carbazole-based polymer chains without needing an additional complementary monomer.
Semiconductor building block synthesis: the pre-installed N-aryl group removes the separate N-arylation step, shortening the overall route toward polymeric and macromolecular semiconductor targets.
Solubility-tuned material design: the single methyl group on the meta-tolyl substituent improves solubility and disrupts overly ordered intermolecular stacking while keeping molecular weight low.

Brand	TCI
CAS number	890653-54-0
Molecular formula	—
Purity	—
Category	Materials Science > Material Building Blocks > Polymer/Macromolecule Semiconductor Building Blocks
Pack sizes	available in standard TCI research-scale packaging; please confirm the required pack size when ordering
Physical form	—
Storage	keep in a tightly closed container under the conditions stated on the manufacturer's label

Chemical name: 3,6-Dibromo-9-(m-tolyl)-9H-carbazole
Product code: D5424

Store the container tightly closed in a cool, dry, and well-ventilated area, away from direct sunlight, heat sources, and incompatible reagents, following the conditions stated on the manufacturer's label and safety data sheet. Keep the material in its original supplier container or in a clean, chemically compatible, well-sealed glass container, clearly labelled with the compound name and CAS number. Handle inside a fume hood while wearing safety glasses, gloves, and a laboratory coat. Avoid generating dust, avoid contact with skin and eyes, and minimise exposure to moisture when transferring material. Close the container promptly after use and dispose of residues and contaminated consumables through the laboratory's chemical waste procedure.

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