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3,3′,5,5′-Tetrabromo-2,2′-bithiophene

CAS Number 125143-53-5

Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers


Product Code B1081-10g
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3,3′,5,5′-Tetrabromo-2,2′-bithiophene

This intermediate is widely used for the synthesis of semiconducting molecules, oligomers and conjugated polymers and more fused aromatic rings.


3,3′,5,5′-Tetrabromo-2,2′-bithiophene has a structure of two thiophenes joined at 2,2'-positions and each is brominated with two bromides at 3,5-positions. This tetra-brominated compound adds functions for further polymerization, cyclisation to form polymers or to add conjugation to the bithiophene unit to form fused rings.

3,3′,5,5′-Tetrabromo-2,2′-bithiophene has been used for the synthesis of dithieno[3,2-b:2′,3′-d]pyrrole, dithieno[3,2-b:2,3-d]silole and their derivatives. Bromides at 3,3'-positions give rise to obtaining fused rings for higher degree of conjugation and flat structures. Polymerization of 3,3′,5,5′-tetrabromo-2,2′-bithiophene and ethynylbenzene monomers via the palladium-catalyzed Sonogashira–Hagihara cross-coupling reaction gives microporous polymers that show ultrahigh absorption performance for iodine vapour with an uptake of up to 345 wt%. Homopolymer poly(N-(2-octyldodecyl)-2,2′-bithiophene-3,3′-dicarboximide), derived from 3,3′,5,5′-tetrabromo-2,2′-bithiophene, exhibits n-channel FET activity and its films exhibit a very high degree of crystallinity and an electron mobility >0.01 cm2 V-1s-1 with a current on−off ratio of 107.

3,3′,5,5′-Tetrabromo-2,2′-bithiophene can be obtained by direct bromination of 2,2'-bithiophene with bromine in chloroform and acetic acid. N-Bromosuccinimide (NBS) can also be used as the oxidising agent to replace bromine for the synthesis. By refluxing 3,3′,5,5′-Tetrabromo-2,2′-bithiophene with zinc in hydrogen chloride and acetic acid, it gives 3,3'-dibromobithiophene.

General Information

CAS Number 125143-53-5
Chemical Formula C8H2Br4S2
Full Name 3,3′,5,5′-Tetrabromo-2,2′-bithiophene
Molecular Weight 481.85 g/mol
Synonyms 3,5-dibromo-2-(3,5-dibromo-2-thienyl)thiophene
Classification / Family Bithiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

3,3′,5,5′-Tetrabromo-2,2′-bithiophene chemical structure
3,3′,5,5′-Tetrabromo-2,2′-bithiophene chemical structure, CAS 125143-53-5

Product Details

Purity >98% (1H NMR in CDCl3)
Melting Point 144.0 °C
Appearance Light yellow to white/off white powder/crystals

MSDS Documentation

3,3′,5,5′-tetrabromo-2,2′-bithiophene MSDS3,3′,5,5′-Tetrabromo-2,2′-bithiophene MSDS Sheet

Literature and Reviews

  1. Synthesis and Properties of Alternating Copolymers Based on 4H-Cyclopenta[2,1-b:3,4-b']dithiophene and 4H-Dithieno[3,2-b:2',3'-d]silol, F. Drozdov et al., Polym. Sci. Ser. B 61, 56–76 (2019); DOI: 10.1134/S1560090419010032.
  2. Novel thiophene-bearing conjugated microporous polymer honeycomb-like porous spheres with ultrahigh iodine uptake, F. Ren et al., Chem. Commun., 52, 9797-9800 (2016); DOI: 10.1039/c6cc05188j.
  3. Two-photon absorption chromophores with a tunable [2,2']bithiophene core, C. Chou et al., Tetrahedron, 62, 8467–8473 (2006); DOI: 10.1016/j.tet.2006.06.085.
  4. Dithiophene-Fused Oxadiborepins and Azadiborepins: A New Class of Highly Fluorescent Heteroaromatics, M. Crumbach et al., Angew. Chem. Int. Ed., 60, 9290 – 9295 (2021); DOI: 10.1002/anie.202100295.
  5. Photovoltaic-Active Dithienosilole-Containing Polymers, L. Liao et al., Macromolecules, 40, 9406-9412 (2007); DOI: 10.1021/ma071825x.
  6. Dialkylthienosilole and N-alkyldithienopyrrole-based copolymers: Synthesis, characterization, and photophysical study, A. El-Shehawy et al., J Phys Org Chem., e4063 (2020); DOI: 10.1002/poc.4063.
  7. Extended conjugated mesogens: synthesis and mesomorphic properties of H-shaped mesogens based on 3,3ʹ,5,5ʹ-tetrasubstituted 2,2ʹ-bithiophene with oligo(1,4-phenyleneethynylene) arms, T. Yatabe et al., Liq. Cryst., 43 (10), 1375-1389 (2016); DOI: 10.1080/02678292.2016.1175674.
  8. Synthesis, Structures, and Electronic Properties of Dithienosiloles Bearing Bulky Aryl Groups: Conjugation between a π-Electron System and “Perpendicular” Aryl Groups, A. Tsurusaki et al., Asian J. Org. Chem., 6 (6), 737-745 (2016); DOI: 10.1002/ajoc.201700058.
  9. n-Channel Polymers by Design: Optimizing the Interplay of Solubilizing Substituents, Crystal Packing, and Field-Effect Transistor Characteristics in Polymeric Bithiophene-Imide Semiconductors, J. Letizia et al., J. Am. Chem. Soc., 130, 30, 9679–9694 (2008); DOI: 10.1021/ja710815a.

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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