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Description
TCI D2657 3,5-Dimethoxybenzyl Bromide is an aromatic alkylating reagent that carries a benzyl bromide group as its reactive centre, flanked by two methoxy groups at positions 3 and 5 of the benzene ring. As a benzyl halide, this compound is a highly effective electrophile for introducing the 3,5-dimethoxybenzyl fragment into a target molecule. In the laboratory, its principal role is as a reagent for forming carbon–heteroatom and carbon–carbon bonds, for example in the alkylation of phenols, alcohols, amines, thiols, and stabilised carbanions.
The properties that make it a preferred choice are its high benzylic reactivity, which stems from the stability of the benzylic cation formed during reaction, together with the electron-donating effect of the two methoxy groups that further stabilise the transition state. As a result, substitution reactions generally proceed rapidly at mild temperatures with a weak base, making the reagent well suited to sensitive substrates. The 3,5-dimethoxy substitution pattern is also characteristic of the skeleton of many natural products in the stilbene and polyketide classes, so this fragment is frequently required intact in total synthesis design.
In Indonesian laboratories, this building block is typically used in synthetic organic chemistry and natural product research groups, where the 3,5-dimethoxybenzyl fragment is installed as part of a planned multi-step route. It serves both academic laboratories pursuing total synthesis targets and applied research groups preparing intermediates and analogues. Where required, the methoxy groups can be opened to the corresponding phenol at a late stage of the sequence.
Laboratory Applications
- Alkylation of phenols: the high benzylic reactivity allows the 3,5-dimethoxybenzyl group to be attached to phenolic oxygen quickly under mild conditions with a weak base.
- Alkylation of alcohols: the reagent acts as an effective electrophile for forming benzylic ether linkages, introducing the fragment onto hydroxyl groups within a target molecule.
- N-alkylation of amines: as a reactive benzyl halide, it transfers the 3,5-dimethoxybenzyl fragment onto nitrogen to build substituted amine intermediates in synthetic sequences.
- S-alkylation of thiols: the electrophilic benzylic carbon reacts readily with sulfur nucleophiles, giving benzylic thioether products without demanding forcing reaction conditions.
- Carbon–carbon bond formation with stabilised carbanions: the reagent alkylates stabilised carbon anions, extending a carbon skeleton with the 3,5-dimethoxybenzyl unit for total synthesis work.
Specifications
- Brand: TCI
- Product code: D2657
- CAS number: 877-88-3
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Chemical name: 3,5-Dimethoxybenzyl Bromide
- Pack sizes: available in standard TCI research-scale packaging; please refer to the catalogue listing for available sizes
- Storage note: store in a cool, dry place in a tightly closed container, protected from moisture
Handling and Storage
Store the reagent in a cool, dry, well-ventilated area inside a tightly closed container, kept away from moisture and from incompatible nucleophilic materials. The original manufacturer's container is the most suitable choice; where transfer is necessary, use clean, dry, chemically compatible glassware with a secure closure and clear labelling. As a reactive benzyl halide, the compound is an alkylating agent and should be handled only in a fume hood, using safety glasses, gloves, and a laboratory coat. Avoid inhalation of vapour or dust and avoid contact with skin and eyes. Keep the container closed when not in use to limit exposure to atmospheric moisture, and consult the manufacturer's safety data sheet before use, following local laboratory waste procedures for disposal of residues.
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