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470864

Sigma-Aldrich

Bromine

≥99.99% trace metals basis

Synonym(s):

Dibromine

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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:
12352101
PubChem Substance ID:
24870690
NACRES:
NA.22

vapor density

7.14 (vs air)

vapor pressure

175 mmHg ( 20 °C)
671 mmHg ( 55 °C)

Assay

≥99.5% (by Na2S2O3, titration)
≥99.99% trace metals basis

resistivity

7.8E18 μΩ-cm, 20°C

impurities

≤0.001% I2
≤0.001% S compounds
<100 ppm total metallic impurities

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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Application

Bromine can be used as a brominating and oxidizing agent in chemical synthesis.
It can be used:
  • To brominate alkylbenzenes at the benzylic position using photocatalytic conditions.
  • To prepare brominated aromatic compounds by electrophilic aromatic substitution reactions in the presence of Lewis acid catalysts.
  • For the bromination of carbonyl compounds at a carbonyl group via Hell-Volhard-Zelinski reaction in the presence of phosphorus trihalides.
  • To prepare isocyanates, carbamates, or amines by reacting with primary amides in the presence of base via Hofmann rearrangement.

Other Notes

Contains organic bromine 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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN5393
MKCK4524
SHBJ1858
SHBH0021V
SZBG0040V

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Bromine
Goehring RR
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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
Kimberly T Barrett et al.
Journal of the American Chemical Society, 135(8), 2963-2966 (2013-02-16)
We report the enantioselective synthesis of atropisomeric benzamides employing catalytic electrophilic aromatic substitution reactions involving bromination. The catalyst is a simple tetrapeptide bearing a tertiary amine that may function as a Brønsted base. A series of tri- and dibrominations were
John D Sivey et al.
Environmental science & technology, 47(3), 1330-1338 (2013-01-18)
HOBr, formed via oxidation of bromide by free available chlorine (FAC), is frequently assumed to be the sole species responsible for generating brominated disinfection byproducts (DBPs). Our studies reveal that BrCl, Br(2), BrOCl, and Br(2)O can also serve as brominating
Bromine-77 and iodine-123 radiopharmaceuticals.
G Stöcklin
The International journal of applied radiation and isotopes, 28(1-2), 131-147 (1977-01-01)
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