3,6-Dibromo-9-(4-methoxyphenyl)-9H-carbazole TCI D5340

Chemical Identity

CAS No.: 746651-52-5
PubChem: CID 58620860·SID 354335420
Formula: C19H13Br2NO
Molecular weight: 431.13 g/mol
Purity: >98.0%(HPLC)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 3,6-dibromo-9-(4-methoxyphenyl)carbazole
SMILES: COC1=CC=C(C=C1)N2C3=C(C=C(C=C3)Br)C4=C2C=CC(=C4)Br
InChIKey: YXWHLCSWBLHWCH-UHFFFAOYSA-N

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TCI D5340 3,6-Dibromo-9-(4-methoxyphenyl)-9H-carbazole is a carbazole-based monomer carrying two bromine atoms at the 3 and 6 positions together with a 4-methoxyphenyl group attached to the nitrogen atom. In the laboratory, this compound serves as a building block for polymer semiconductors — a starting material designed to be linked repeatedly into conjugated macromolecular chains. The two symmetrically placed bromine atoms act as reactive connection points, allowing researchers to construct polymers with controlled chain length and architecture without having to modify the carbazole core beforehand.

The characteristics that make this compound a frequent choice are the symmetry of its bromine positions and the electronic behaviour of the methoxyphenyl group on the nitrogen. Positions 3 and 6 are the most reactive sites on the carbazole core, so cross-coupling reactions such as Suzuki–Miyaura and Stille, as well as Yamamoto-type polymerisation, can proceed with good selectivity. The methoxy group on the phenyl ring is electron-donating and raises the electron density of the conjugated system, while at the same time providing a spectroscopic marker that is easy to recognise during characterisation by nuclear magnetic resonance.

In Indonesian laboratories, this monomer is typically handled in university and institutional research groups working on organic electronic materials, where conjugated polymers are synthesised on a small scale before being characterised and processed into thin films. It is generally used in reaction setups under an inert atmosphere, weighed out in modest quantities per experiment, and stored alongside other coupling partners and catalyst systems so that a planned polymerisation series can be run consistently from one batch.

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Conjugated polymer synthesis — the two bromine atoms at positions 3 and 6 give symmetric, equally reactive connection points, so chains grow in a predictable linear fashion rather than branching unpredictably.
Suzuki–Miyaura cross-coupling — the aryl bromide positions react selectively with boronic acid or boronate partners, letting researchers pair the carbazole unit with a wide range of co-monomers.
Stille coupling — the same brominated sites couple with organotin reagents, which is useful when the chosen co-monomer is more conveniently prepared as a stannane than as a boronate.
Yamamoto-type polymerisation — direct reductive coupling of the two carbon–bromine bonds produces homopolymers of the carbazole unit without requiring a second, separately functionalised monomer.
Electron-rich material design — the methoxy group on the N-phenyl ring donates electron density into the conjugated system, allowing deliberate tuning of the electronic character of the resulting polymer.

Brand	TCI
CAS number	746651-52-5
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 size when ordering
Physical form	—
Storage	keep in the closed original container under the conditions stated on the product label and accompanying documentation

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

Store the material in its tightly closed original container, in a cool, dry and well-ventilated area away from direct sunlight, moisture and sources of ignition, following the storage conditions stated on the manufacturer's label and safety data sheet. Amber glass or the supplied original packaging is suitable for keeping the solid protected from light and humidity. Handle in a fume hood using gloves, safety glasses and a laboratory coat, and weigh the solid carefully to avoid generating dust. Keep it separate from strong oxidising agents, close the container promptly after use, and dispose of residues and contaminated materials as chemical waste according to institutional procedures.

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