230367

Boron tribromide

≥99.99%

• Synonym(s): Tribromoboron
• Empirical Formula (Hill Notation): BBr₃
• CAS Number: 10294-33-4
• Molecular Weight: 250.52
• EC Number: 233-657-9
• MDL number: MFCD00011312
• UNSPSC Code: 12352101
• PubChem Substance ID: 24853799
• NACRES: NA.22

Properties

• vapor density: 8.6 (vs air)
• vapor pressure: 40 mmHg ( 14 °C)
• assay: ≥99.99%
• form: liquid
• bp: ~90 °C (lit.)
• mp: −46 °C (lit.)
• density: 2.60 g/mL at 20 °C (lit.)
• SMILES string: BrB(Br)Br
• InChI: 1S/BBr3/c2-1(3)4
• InChI key: ILAHWRKJUDSMFH-UHFFFAOYSA-N

Description

General description

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.

Application

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.

Safety Information

• pictograms: GHS06,GHS05
• signalword: Danger
• hcodes: H300 + H330,H314
• pcodes: P260 - P271 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1A
• Storage Class: 6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter