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230367

Sigma-Aldrich

Boron tribromide

≥99.99%

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Synonym(s):
Tribromoboron
Empirical Formula (Hill Notation):
BBr3
CAS Number:
Molecular Weight:
250.52
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

8.6 (vs air)

Quality Level

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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This Item
419508211222202207
Boron tribromide ≥99.99%

Sigma-Aldrich

230367

Boron tribromide

Boron tribromide ReagentPlus®, ≥99%

Sigma-Aldrich

419508

Boron tribromide

Boron tribromide ReagentPlus®, 99.9%

Sigma-Aldrich

202207

Boron tribromide

form

liquid

form

-

form

liquid

form

-

bp

~90 °C (lit.)

bp

~90 °C (lit.)

bp

-

bp

~90 °C (lit.)

mp

−46 °C (lit.)

mp

−46 °C (lit.)

mp

-

mp

−46 °C (lit.)

density

2.60 g/mL at 20 °C (lit.)

density

2.60 g/mL at 20 °C (lit.)

density

1.467 g/mL at 25 °C

density

2.60 g/mL at 20 °C (lit.)

vapor density

8.6 (vs air)

vapor density

8.6 (vs air)

vapor density

-

vapor density

8.6 (vs air)

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

Pictograms

CorrosionSkull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1A

Storage Class Code

6.1A - 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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Customers Also Viewed

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Ether Cleavage Re-Investigated: Elucidating the Mechanism of BBr3-Facilitated Demethylation of Aryl Methyl Ethers
Kosak TM, et al.
European Journal of Organic Chemistry, 2015(34), 7460-7467 (2015)
Tetrahedron Letters, 34, 3071-3071 (1993)
Michael S. Lube et al.
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)
Boron trichloride/tetra-n-butylammonium iodide: A mild, selective combination reagent for the cleavage of primary alkyl aryl ethers
Brooks PR, et al.
The Journal of Organic Chemistry, 64(26), 9719-9721 (1999)

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