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2-Bromo-5-dodecylthiophene

CAS Number 153561-74-1

Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers


Product Code B1531-LT-1g
Price $95 ex. VAT

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Another widely used alkylated thiophenes

Offers great solubility, thermal stability, and film morphology in application of OFETs and OPVs


2-Bromo-5-dodecylthiophene, bearing a dodecyl alkyl chain (C12H25) and a bromo function group at both end positions of the thiophene ring, is widely used for the synthesis of semiconducting small molecules, oligomers, and conjugated polymers in the application of organic electronics.

2-Bromo-5-dodecylthiophene is obtained by reacting 5-dodecylthiophene with N-Bromosuccinimide (NBS). The end bromo group provides the functionality for cross coupling or nucleophilic aromatic substitution reactions to offer extended conjugation to the targeted molecules. The long dodecyl alkyl chain offers great solubility thus improves the processability for organic electronics in solutions. Typically, with dodecyl being on the end of the thiophene ring, 2-bromo-5-dodecylthiophene is used as an end-capper especially in the case of OFETs materials.

2-Bromo-5-dodecylthiophene has also been presented in the synthesis of semiconducting calamitic and discotic liquid crystals, owing to the flexible long alkyl chain and the rigid thiophene/phenylene core.

General Information

CAS Number 153561-74-1
Chemical Formula C16H27BrS
Full Name 2-Bromo-5-dodecylthiophene
Molecular Weight 311.35 g/mol
Synonyms N/A
Classification / Family Thiophene derivatives, Dyes, Semiconductor synthesis intermediates, OLED, OFETs, organic photovoltaics

Chemical Structure

2-Bromo-5-dodecylthiophene chemical structure, CAS 153561-74-1

Product Details

Purity N/A
Boiling Point Tb = 371.2±22.0 °C at 760 mmHg
Appearance Yellow liquid

MSDS Documentation

2-Bromo-5-dodecylthiophene2-Bromo-5-dodecylthiophene MSDS Sheet

Literature and Reviews

  1. Asymmetric alkythienyl thienoacenes derived from anthra[2,3-b]thieno[2,3-d]thiophene for solution-processable organic semiconductors, Y. Ogawa et al., ACS Appl. Mater. Interfaces, 9, 9902−9909(2017); DOI: 10.1021/acsami.6b15793.
  2. Bent-core mesogens with thiophene units, K. Geese et al., J. Mater. Chem., 20, 9658–9665(2010); DOI: 10.1039/C0JM01919D.
  3. Influence of conjugation axis on the optical and electronic properties of aryl-substituted benzobisoxazoles, B. Tlach et al., J. Org. Chem., 78(13), 6570–6581(2013); DOI: 10.1021/jo4007927.
  4. Near-infrared fluorescent thienothiadiazole dyes with large stokes shifts and high photostability, Y. Zhang et al., J. Org. Chem., 82(11), 5597–5606(2017);DOI: 10.1021/acs.joc.7b00422.
  5. Small asymmetric anthracenethiophene compounds as organic thin-film transistors, B. Shaik et al., Tetrahedron, 69, 8191-8198(2013); DOI: 10.1016/j.tet.2013.07.041.
  6. Two-dimensional nanostructures by the assembly of n-type tetraazaanthracene-based conjugated molecules, C. He et al., Chem. Phy. Chem., 14(13), 2954-2960(2013); DOI: 10.1002/cphc.201300444.

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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