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419508

Sigma-Aldrich

Boron tribromide

ReagentPlus®, ≥99%

Synonym(s):

Tribromoboron

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About This Item

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:
24866111
NACRES:
NA.22

vapor density

8.6 (vs air)

vapor pressure

40 mmHg ( 14 °C)

product line

ReagentPlus®

Assay

≥99%

color

colorless to amber

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 is a strong Lewis acid generally employed in the deprotection of -OH and -NH groups. It is a moisture-sensitive liquid, which is also used to cleave esters or ethers into alkyl bromides.

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
Used to cleave aryl methyl ethers in a synthesis of a benzopyranobenzopyran from a coumarin scaffold.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H300 + H330,H314

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Boron Tribromide
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2006)
Boron Halides
Kirk-Othmer Encyclopedia of Chemical Technology (2003)
Qing Zhao et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 203, 472-480 (2018-06-15)
Four homo/heterometallic complexes [Cu3(L)(μ2-OAc)9(CH3OH) 9]·3CHCl3 (1), [Cu2(L)Ca(μ2-NO3)9] (9), [{Cu2(L)Sr(μ2-NO3)9}9]·CH3CH2OH (11) and [Cu2(L)Ba(μ2-OAc)9(OAc)] (14), containing an acyclic naphthalenediol-based ligand H4L, were synthesized and characterized by elemental analyses, IR, UV-Vis, fluorescence spectra, TG-DTA and X-ray crystallography. The complex 1 was obtained by
Tetrahedron Letters, 47, 5909-5909 (2006)
Hui Wang et al.
European journal of medicinal chemistry, 88, 66-73 (2014-09-14)
The pharmacokinetics (PK) and pharmacodynamics (PD) of PT119, a potent Staphylococcus aureus enoyl-ACP reductase (saFabI) inhibitor with a Ki value of 0.01 nM and a residence time of 750 min on the enzyme target, has been evaluated in mice. PT119
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