Tetrabromothiophene

CAS Number 3958-03-0

Chemistry Building Blocks, Heterocyclic Building Blocks, Materials, Monomers

A fully brominated thiophene and a useful building block

Used for the synthesis of thiophene and fused thiophene derivatives in application of OFETs and OPVs.

Specifications | MSDS | Literature and Reviews

Tetrabromothiophene (CAS number 3958-03-0) is a fully brominated thiophene. Fully functionalised around the thiophene ring, tetrabromothiophene is used for the construction of further conjugated semiconductors as thiophene, fused thiophene or poly-fused thiophene structures in application of organic electronics, i.e. polymer solar cells and organic field-effect transistors. Fused thieno[3,2-b:4,5-b’]diindoles can be prepared with tetrabromothiophene as the starting material. Tetrabromothiophene is also an intermediate for the preparation of 3,4-dibromothiophene.

Derived from tetrabromothiophene, TPTn and TPTEn, both bearing one tetraphenylthiophene-core and either peripheral alkoxyl chains or 3,4,5-trialkoxybenzoate groups, form square, rectangular or hexagonal columnar phases depending on the mesogenic core structures and the chain length of aliphatic tails. Besides, TPTn and TPTEn luminescent liquid crystal molecules show obvious aggregation-induced emission (AIE) characteristics, the fluorescence emission intensity values measured in the aggregated state were hundred times higher than those values measured in benign solvents [1].

General Information

CAS Number	3958-03-0
Chemical Formula	C₄Br₄S
Full Name	Tetrabromothiophene
Molecular Weight	399.72 g/mol
Synonyms	2,3,4,5-tetrabromothiophene, Perbromothiophene
Classification / Family	Thiophenes, Semiconductor synthesis intermediates, Low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Melting point	T_m= 115 °C
Appearance	Off-white to orange/brown powder/crystals

MSDS Documentation

Tetrabromothiophene MSDS Sheet

Literature and Reviews

Luminescent liquid crystals bearing an aggregation-induced emission active tetraphenylthiophene fluorophore, L. Guo et al., J. Mater. Chem. C, 7, 4828-4837 (2019); DOI: 10.1039/C9TC00448C.
Regioselective Palladium(0)-Catalyzed Cross-Coupling Reactions and Metal-Halide Exchange Reactions of Tetrabromothiophene: Optimization, Scope and Limitations, Đ. Tùng et al., Adv. Synth. Catal., 25 (10), 1595-1609 (2009); DOI: 10.1002/adsc.200900044.
Photodissociation dynamics of halogenated aromatic molecules: the case of core-ionized tetrabromothiophene, L. Pihlava et al., Phys. Chem. Chem. Phys., 23, 21249-21261 (2021); DOI: 10.1039/D1CP03097C.

Measurement and correlation of the solubility of 2,3,4,5-tetrabromothiophene in different solvents, K. Wang et al., J. Chem. Thermodyn., 55, 50-55 (2012); DOI: 10.1016/j.jct.2012.06.005.
Composition tuning of a mixture of thienothiophene-based polymer (PTB7) and PC70BM using a novel additive, tetrabromothiophene (Br-ADD), G. Kim et al., Org. Electron., 15 (11), 3268-3273 (2014); DOI: 10.1016/j.orgel.2014.07.038.
Halogen dance reactions—A review, M. Schnürch et al., Chem. Soc. Rev., 36, 1046-1057 (2007); DOI: 10.1039/B607701N.
A Star-Shaped Supercrowded 2,3,4,5-Tetraferrocenylthiophene: Synthesis, Solid-State Structure, and Electrochemistry, A. Hildebrandt et al., Organometallics, 29, 4900–4905 (2010); DOI: 10.1021/om1001099.
Efficient synthesis of thieno[3,2-b:4,5-b′]diindoles and benzothieno[3,2-b]indoles by Pd-catalyzed site-selective C–C and C–N coupling reactions, T. Hung et al., Org. Biomol. Chem., 10, 9041-9044 (2012); DOI: 10.1039/C2OB26489G.
Synthesis of Dibenzothiophenes and Carbazoles by Sequential ‘Tetra-Fold Heck/6 π-Electrocyclization/Dehydrogenation’ Reactions of Tetrabromothiophene and Tetrabromo-N-methylpyrrole, S.-M. Toguem et al., Adv. Synth. Catal., 354, 1819 – 1826 (2012); DOI: 10.1002/adsc.201200057