4-(2-decyloxypyrimidin-5-yl)phenol

Description

4-(2-decyloxypyrimidin-5-yl)phenol is a pyrimidine-based building block bearing a decyloxy chain. Ring heteroatoms redistribute electron density, dipole and hydrogen-bonding capacity relative to an all-carbon analogue – which is the reason a heterocyclic core gets chosen where a carbocycle would be geometrically equivalent but electronically wrong.

Key data

• Molecular formula: C20H28N2O2
• Molecular weight: 328.45 g/mol
• Category: Heterocycles

What the substitution pattern does

The decyloxy chain places this compound at n=10 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.

The chain is attached through oxygen rather than directly to the ring. That ether linkage conjugates the oxygen lone pair into the aromatic system, raising polarisability along the molecular axis and typically lifting transition temperatures above those of the directly bonded alkyl analogue.

Two ring nitrogens give pyrimidine a substantial in-plane dipole and remove electron density from the ring. Both effects are exploited deliberately: the dipole couples to applied fields, and the electron deficiency activates the ring toward nucleophilic substitution at the 2- and 4-positions.

Typical applications

• smectic-phase studies where a long terminal chain is required
• materials chemistry requiring a polar, planar ring system
• heterocyclic cores for mesogens with tailored dipole and polarisability
• ligand and pharmacophore construction in discovery chemistry
• fluorescent probes and laser dyes where the coumarin motif applies

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.

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.