Boron tribromide (BBr3) is a strong Lewis acid generally used as a reagent for the deprotection of ethers. Alkyl aryl ethers are cleaved at the alkyl-oxygen bond to give ArOH and alkyl bromides. In a particular case, BBr3 was used to cleave acetals that could not be deprotected under standard acidic conditions. Similarly, amino acid-protecting groups such as benzyloxycarbonyl and tert-butoxycarbonyl groups can be deprotected by BBr3. It can also be used to deprotect carbohydrate derivatives and polyoxygenated intermediates in the preparation of deoxyvernolepin, vernolepin, and vernomenin.
Reactant for preparation of:
- Drug intermediate 6-nitro-L-DOPA
- Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties
- High-quality boron-doped graphene via Wurtz-type reductive coupling reaction
- Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities
- Micrometer-sized organic molecule-DNA hybrid structures
- Borane complexes via electrophilic aromatic borylation reactions
- A 5-HT2C receptor agonist
- Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease
- A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit
- Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides
With alkynes forms 2-alkenyldibromoboranes, which show reversed regiochemistry in Diels-Alder reactions as compared to BBN. Intermediates generated from 1-alkynes couple to alkyl halides providing trisubstituted alkenes. Reacts with chiral sulfonamides to provide precursors of chiral glycidol esters, acetate diols, β-hydroxy esters, and amino acid esters. Useful for the synthesis of precursors to group 13-15 semiconductor materials.