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3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole

CAS Number 173063-52-0

Chemistry Building Blocks, Dibromo Monomers, Monomers


Product Code B3671-1g
Price $69 ex. VAT

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A dibromo-substituted 2-ethylhexyl-carbazole building block

serves as a monomer in the preparation of organic semiconducting materials for use in solar cells and OLEDs


3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole (CAS number 173063-52-0) is a carbazole derivative bearing two bromide groups at 3 and 6-positions as well as a 2-ethylhexyl group at the 9-position. The bromo-substituents enable 3,6-dbromo-9-(2-ethylhexyl)-9H-carbazole to undergo facile reactions, including Suzuki coupling reactions and Kumada polymerisation. A carbazole copolymer, linked at the position 2,7 and 3,6, is synthesised by combining 3,6-dibromo-9-(2-ethylhexyl)-9H-carbazole with 2,7-dipinacol-(2-ethylhexyl)-9H-carbazole. The resulting carbazole copolymer possesses a wide band gap of 3.2 eV and displays a narrow emission band at 400 nm (with a full width half maximum of 56 nm).

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Versatile building block 173063-52-0

Versatile building block

works in different reactions

Synthetic monomer 173063-52-0

Synthetic monomer

Synthetic monomer for HTL materials (in OPVs and OLEDs)

A novel copolymer of fluorene and carbazole, known as PF8Cz (poly[(9,9-dioctylfluorenyl-2,7-diyl)-alt-(9-(2-ethylhexyl)-carbazole-3,6-diyl)]) can be prepared from 3,6-dibromo-9-(2-ethylhexyl)-9H-carbazole and 2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane). PF8Cz has an optical bandgap of 3.06 eV, widely used as a hole-transport layer (HTL) material in OLEDs.

General Information

CAS Number 173063-52-0
Chemical Formula C20H23Br2N
Full Name 3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole
Molecular Weight 437.22 g/mol
Synonyms 3,6-Dibromo-N-(2-ethylhexyl)carbazole, 9-(2’-Ethylhexyl)-3,6-dibromo carbazole
Classification / Family Carbazole building blocks, Bromide ligands, Organic photovoltaics, Polymer solar cells, Perovskite solar cells, Polycarbazoles, OLEDs, Hole-transport layers, Organic semiconducting materials

Chemical Structure

3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole chemical structure, CAS 173063-52-0.
3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole chemical structure, CAS 173063-52-0

Product Details

Purity 98%
Melting Point N/A
Appearance Colourless to pale yellow liquid

MSDS Documentation

3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole MSDS Sheet

Literature and Reviews

  1. Alternating 2,7- and 3,6-linked carbazole copolymers as wide band gap energy transfer donors, D. Pickup et al., The Solid Films, 517(9), 2840–2844(2009); DOI: 10.1016/j.tsf.2008.10.044.
  2. Carbazole-functionalized polyfluorenes: synthesis and conformational properties in chloroform solution and β-phase formation in copolyfluorene films, M. Simonova et al., Mater. Today Chem., 22, 100553(2021); DOI: 10.1016/j.mtchem.2021.100553.
  3. Efficient synthesis of well-defined polycarbazoles via catalyst-transfer Kumada coupling polymerization, H. Wen et al., Eur. Polym. J., 49(11), 3740–3743(2013); DOI: 10.1016/j.eurpolymj.2013.08.016.
  4. 3,6-Linked 9-alkyl-9H-carbazole main-chain polymers: preparation and properties, A. Iraqi et al., J. Polym. Sci., Part A: Polym. Chem., 42, 6041–6051(2004); DOI: 10.1002/pola.20420.
  5. Highly efficient light-emitting diodes based on self-assembled colloidal quantum wells, Y. Zhu et al., Adv. Mater., 2305382(2023). DOI: 10.1002/adma.202305382.
  6. Solution-processed green and blue quantum-dot light-emitting diodes with eliminated charge leakage, Y. Deng et al., Nat. Photonics, 16, 505–511(2022); DOI: 10.1038/s41566-022-00999-9.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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