230367
Boron tribromide
≥99.99%
Synonym(s):
Tribromoboron
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About This Item
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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
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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.
accessory
Product No.
Description
Pricing
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Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1A
Storage Class Code
6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Inorganic chemistry, 35(17), 5007-5014 (1996-08-14)
The 1:1 mole ratio reactions of boron trihalides (BX(3)) with tris(trimethylsilyl)phosphine [P(SiMe(3))(3)] produced 1:1 Lewis acid/base adducts [X(3)B.P(SiMe(3))(3), X = Cl (1), Br (2), I (5)]. Analogous 1:1 mole ratio reactions of these boron trihalides with lithium bis(trimethylsilyl)phosphide [LiP(SiMe(3))(2)] produced
Tetrahedron Letters, 29, 1811-1811 (1988)
Tetrahedron Letters, 34, 3071-3071 (1993)
Tetrahedron Letters, 32, 2857-2857 (1991)
Boron Tribromide
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 2015(34), 7460-7467 (2001)
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