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277576

Sigma-Aldrich

Bromine

ACS reagent, ≥99.5%

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About This Item

Empirical Formula (Hill Notation):
Br2
CAS Number:
7726-95-6
Molecular Weight:
159.81
EC Number:
231-778-1
MDL number:
MFCD00010896
UNSPSC Code:
12141915
PubChem Substance ID:
329753018
NACRES:
NA.21

grade

ACS reagent

vapor density

7.14 (vs air)

vapor pressure

175 mmHg ( 20 °C)
671 mmHg ( 55 °C)

Assay

≥99.5%

form

liquid

resistivity

7.8E18 μΩ-cm, 20°C

impurities

organic bromine compounds, passes test
≤0.001% I2
≤0.001% S compounds

evapn. residue

≤0.005%

bp

58.8 °C (lit.)

mp

−7.2 °C (lit.)

density

3.119 g/mL at 25 °C (lit.)

anion traces

chloride (Cl-): ≤0.05%

cation traces

Ni: ≤5 ppm
heavy metals: ≤2 ppm

SMILES string

BrBr

InChI

1S/Br2/c1-2

InChI key

GDTBXPJZTBHREO-UHFFFAOYSA-N

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General description

Bromine is a highly volatile and reactive halogen that can be used as a powerful brominating and oxidizing agent in chemical synthesis.

Application

Bromine can be used as a brominating agent for the bromination of:
  • Aromatic and heterocyclic compounds. 
  • Carbonyl compounds at α position to carbonyl groups.
  • Aromatic carboxylic acids via Hell-Volhard-Zelinski reaction in the presence of phosphorus trihalides.
  • Alkylbenzenes at the benzylic position using photocatalytic conditions.

It can also be used as an oxidizing agent for the oxidation of:
  • Primary alcohols to either aldehydes or esters.      
  • Secondary alcohols to ketones.

It can also be used as a Lewis acid catalyst to:     
  • Convert epoxides and CO2 to cyclic carbonates in a continuous flow system.     
  • Synthesize bis(indolyl)methanes by reacting indoles with carbonyl compounds.

Signal Word

Danger

Hazard Statements

H314,H330,H400

Hazard Classifications

Acute Tox. 1 Inhalation - Aquatic Acute 1 - 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 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Reaction of bromine and chlorine with phenolic compounds and natural organic matter extracts-Electrophilic aromatic substitution and oxidation.
Criquet J, et al.
Water Research, 85, 476-486 (2015)
The chemistry of atmospheric bromine.
Wofsy SC, et al.
Geophysical Research Letters, 2(6), 215-218 (1975)
Bromine-catalyzed aziridination of olefins. A rare example of atom-transfer redox catalysis by a main group element.
Jeong JUK, et al.
Journal of the American Chemical Society, 120(27), 6844-6845 (1998)
Jennifer A Kozak et al.
Journal of the American Chemical Society, 135(49), 18497-18501 (2013-11-22)
A continuous method for the formation of cyclic carbonates from epoxides and carbon dioxide (CO2) is described. The catalysts used are inexpensive and effective in converting the reagents to the products in a residence time (t(R)) of 30 min. The
Vitalij V Levin et al.
Organic letters, 15(4), 917-919 (2013-02-02)
Reactions of difluorocarbene with benzyl and alkylzinc halides leading to fluorinated organozinc species have been described. The generated α-difluorinated organozinc reagents are reasonably stable in solution and can be quenched with external electrophiles (iodine, bromine, proton), affording compounds containing the
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