2,7-Dibromo-9-vinyl-9H-carbazole TCI D5425

Chemical Identity

Other names: 2,7-Dibromo-9-ethenyl-9H-carbazole
CAS No.: 1438252-33-5
PubChem: CID 101342828·SID 468591347
Formula: C14H9Br2N
Molecular weight: 351.04 g/mol
Purity: >98.0%(GC)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 2,7-dibromo-9-ethenylcarbazole
SMILES: C=CN1C2=C(C=CC(=C2)Br)C3=C1C=C(C=C3)Br
InChIKey: AQVAIVOLMNGCLU-UHFFFAOYSA-N

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TCI D5425, chemically known as 2,7-Dibromo-9-vinyl-9H-carbazole (CAS 1438252-33-5), is an organic semiconductor molecule that combines two distinct types of reactive groups in a single structure. Its carbazole core carries bromine atoms at the 2- and 7-positions, while the nitrogen atom bears a vinyl group. The compound is classified as a small molecule semiconductor building block and serves in the laboratory as a versatile precursor, used both for constructing conjugated frameworks through cross-coupling chemistry and for forming polymers through addition reactions at its vinyl double bond.

What makes this compound distinctive is the placement of the bromides at the 2- and 7-positions. Unlike the more common 3,6-substitution pattern, linkage at the 2- and 7-positions extends conjugation along the long axis of the carbazole core, so the resulting polymers or oligomers tend to exhibit more widely delocalised electrons. This property is frequently exploited when researchers wish to shift optical absorption toward longer wavelengths or to tune the band gap of a material. The vinyl group on the nitrogen adds a second, entirely different synthetic pathway — radical polymerisation — allowing a single material to serve two separate material-fabrication strategies.

In Indonesian laboratories, this dual reactivity makes the compound a practical choice for research groups working on organic electronic materials at university and institutional scale. It is typically handled in synthesis laboratories equipped for cross-coupling chemistry and controlled polymerisation, where a single reagent that supports two independent routes reduces the number of separate starting materials that must be sourced, stored, and qualified for a given project.

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Suzuki–Miyaura cross-coupling: the two aryl bromides act as reliable coupling handles for building extended conjugated backbones with boronic acid or ester partners.
Conjugated polymer synthesis: 2,7-linkage extends conjugation along the carbazole long axis, giving polymers with broader electron delocalisation than 3,6-linked analogues.
Radical polymerisation of the vinyl group: the N-vinyl function opens a completely separate chain-growth route to carbazole-containing polymers without touching the bromides.
Band gap and absorption tuning: researchers use the extended 2,7-conjugation pathway to shift optical absorption of the resulting material toward longer wavelengths.
Oligomer and model compound preparation: the defined dibromo substitution pattern allows stepwise construction of well-characterised conjugated oligomers for structure–property studies.

Brand	TCI
CAS number	1438252-33-5
Molecular formula	—
Purity	—
Category	Materials Science > Material Building Blocks > Small Molecule Semiconductor Building Blocks
Pack sizes	research-scale packaging; please refer to the current product listing for available options
Physical form	—
Storage	refer to the manufacturer's label and accompanying documentation for the specified storage conditions

Chemical name: 2,7-Dibromo-9-vinyl-9H-carbazole

Store the container tightly closed in a cool, dry, and well-ventilated place, protected from direct light and from sources of heat or ignition. As with other vinyl-functional monomers, unnecessary warming and prolonged exposure to light should be avoided, and the material should be kept in its original tightly sealed container or an equivalent chemically compatible, light-protecting vessel. Handle in a fume hood using gloves, safety glasses, and a laboratory coat, and avoid generating dust during weighing and transfer. Where the compound is used in moisture- or oxygen-sensitive coupling reactions, transfer under an inert atmosphere is advisable. Always consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated materials in accordance with institutional chemical waste procedures.

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