3-Methylbenzo[b]thiophene is an aromatic heterocyclic compound consisting of a benzene ring fused to a thiophene ring, carrying a methyl group at the three position. The benzothiophene framework is one of the most frequently encountered sulfur heterocyclic motifs in pharmaceutical chemistry and materials chemistry. In the laboratory, this compound serves as a building block for the construction of more complex molecules, and at the same time as a model compound representing the behaviour of aromatic sulfur species in a range of catalysis and fuel processing studies. Supplied by TCI, it belongs to the heterocyclic building blocks group within the chemistry catalogue.
The properties that make this material attractive are the stable aromaticity of the fused system combined with directed reactivity at specific positions. The two position on the thiophene ring is the most reactive site towards deprotonation by organolithium bases as well as towards electrophilic substitution, so selective functionalisation can be carried out using well established procedures. The methyl group at the three position not only increases solubility in organic solvents, but can also be converted by free radical halogenation into a bromomethyl group that is highly useful as an electrophile. The sulfur atom in the ring additionally imparts electronic character to the system.
In Indonesian laboratories, this compound is typically used in university and institutional synthetic chemistry groups, in medicinal chemistry programmes that build sulfur containing scaffolds, and in petroleum and catalysis research units that study aromatic sulfur behaviour. It is normally handled at bench scale in fume hood work, with quantities drawn from a single pack across a series of reactions, and stored alongside other heterocyclic building blocks in a dedicated organic reagent cabinet.
- Heterocyclic scaffold synthesis: the fused benzothiophene core provides a ready made sulfur heterocycle, sparing the researcher a multistep ring construction sequence when building larger target molecules.
- Directed lithiation chemistry: the two position responds cleanly to organolithium bases, allowing chemists to introduce a wide range of substituents through established deprotonation and quenching procedures.
- Electrophilic substitution studies: the same two position is the preferred site for electrophilic attack, making this compound a dependable substrate for teaching and probing aromatic substitution selectivity.
- Side chain functionalisation via radical halogenation: the three methyl group can be converted to a bromomethyl handle, giving access to a reactive electrophile for subsequent alkylation and coupling work.
- Model compound for sulfur behaviour in catalysis and fuel processing: it represents aromatic sulfur species faithfully, so it is widely used in hydrotreating, desulfurisation and catalyst evaluation experiments.
| Brand | TCI |
|---|---|
| CAS number | 1455-18-1 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Heterocyclic Building Blocks |
| Pack sizes | available in standard research quantities; please confirm the currently listed pack options when ordering |
| Physical form | — |
| Storage | keep in a cool, dry place in the tightly closed original container |
- Catalogue code: M1952
Store the container tightly closed in a cool, dry, well ventilated area away from heat, open flame, strong oxidising agents and direct sunlight. The original supplier container is the most suitable vessel; if transfer is necessary, use a clean amber glass bottle with a chemically resistant cap and label it clearly with the name and CAS number. Handle inside a fume hood, since aromatic sulfur compounds carry a persistent odour. Wear safety goggles, nitrile gloves and a laboratory coat, and avoid inhalation or skin contact. Keep the container closed when not in use to limit vapour release, and consult the manufacturer safety data sheet before first use and before disposal of any residues.
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