4-bromooctylbenzene

Description

4-bromooctylbenzene is a functionalised aromatic intermediate carrying an octyl chain.

The aryl bromide is the electrophilic half of the cross-coupling pair: it undergoes oxidative addition to palladium, and it is equally the entry point to halogen-metal exchange when an aryllithium or Grignard reagent is wanted. Bromides are the usual working compromise – reactive enough for standard catalyst systems, cheaper and more robust than the iodides.

Key data

• Catalogue code: KC1030
• CAS number: 51554-93-9
• Molecular formula: C14H21Br
• Molecular weight: 269.22 g/mol
• Category: Aromatics
• Also listed as: 1-(4-Bromophenyl)octane

What the substitution pattern does

The octyl chain places this compound at n=8 in its homologous series. Chain length is not a cosmetic variable here: each added methylene lowers the melting point unevenly and shifts the balance between nematic and smectic order, because a chain with an even number of carbons projects its terminal bond at a different angle to the molecular long axis than an odd one. Homologues therefore alternate in behaviour rather than trending smoothly, and an even-numbered member frequently outperforms both of its neighbours for a given formulation.

At this chain length the aliphatic volume starts to dominate. Long chains favour layered smectic packing over the nematic phase and increase solubility in non-polar media, which matters as much for work-up as for the final material.

Typical applications

• smectic-phase studies where a long terminal chain is required
• precursor to the matching boronic acid or trifluoroborate
• alkyl-chain building block for calamitic mesogens
• general intermediate for fine chemical and materials synthesis
• oxidative-addition partner in palladium-catalysed cross-coupling

Ordering

This compound is supplied to order. Pricing depends on quantity and on the specification you need, so it is quoted rather than listed – send an enquiry stating the quantity and any purity or analytical requirement, and you will receive a written quotation.

Please quote CAS 51554-93-9 or catalogue code KC1030 when enquiring, so that the correct isomer is supplied.

Handling and documentation

Supplied for laboratory and industrial use by trained personnel only. Not for use as a medicine, food, cosmetic or biocide, and not for administration to humans or animals. Safety documentation is issued with the order; this page is not a source of hazard information.