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230367

Boron tribromide

≥99.99%

Synonym(s):

Tribromoboron

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Size/SKUAvailabilityPrice
5 g
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$78.30
25 g
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$119.00
100 g
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$230.00

About This Item

Linear Formula:
BBr3
CAS Number:
Molecular Weight:
250.52
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352101
EC Number:
233-657-9
MDL number:
Assay:
≥99.99%
Form:
liquid

$78.30


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vapor density

8.6 (vs air)

Quality Segment

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

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

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.
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

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This Item
202207211222419508
description

≥99.99%

description

ReagentPlus®, 99.9%

description

1.0 M in methylene chloride

description

ReagentPlus®, ≥99%

assay

≥99.99%

assay

99.9%

assay

-

assay

≥99%

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

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.)

form

liquid

form

-

form

liquid

form

-

bp

~90 °C (lit.)

bp

~90 °C (lit.)

bp

-

bp

~90 °C (lit.)


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Pictograms

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Codes

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

WGK 3

PPE (personal protective equipment)

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter



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Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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