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Key Documents

8.20171

Sigma-Aldrich

Bromine

for synthesis

Synonym(s):

Bromine

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About This Item

CAS Number:
Molecular Weight:
159.81
MDL number:
UNSPSC Code:
12352300
EC Index Number:
231-778-1
NACRES:
NA.22

vapor pressure

233 hPa ( 20 °C)

Quality Level

form

liquid

reaction suitability

reagent type: oxidant

kinematic viscosity

0.314 cSt(20 °C)

bp

58.8 °C/1013 hPa

mp

-7.3 °C

solubility

35 g/L

density

3.12 g/cm3 at 20 °C (liquid)

storage temp.

15-25°C

InChI

1S/BrH/h1H/p-1

InChI key

CPELXLSAUQHCOX-UHFFFAOYSA-M

General description

for synthesis

Application

Bromine can be used as an oxidizing agent for the oxidation of:
  • Primary alcohols to either aldehydes or esters and secondary alcohols to give ketones.
  • Alcohols or diols to tetrahydrofurans in the presence of silver(I) salts.
  • Enediol bis-trimethylsilyl ethers to α-diketones.
  • Aldehydes to esters in the presence of alcohol solvents and sodium bicarbonate buffer.
  • Aliphatic and aromatic thiols to disulfides.

Bromine can also be used along with other co-reactants such as hexamethylphosphoric triamide (HMPA) and bis(tributyltin) oxide (HBD) to selectively oxidize secondary alcohols. However, bromine/nickel carboxylates convert 1,4-diols to γ-butyrolactones by selective oxidation of the primary alcohols.

Analysis Note

Assay (iodometric)≥ 99.0 %AppearanceBrownish-red fuming liquid

Signal Word

Danger

Hazard Statements

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)

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Bromine as an oxidant for direct conversion of aldehydes to esters
Williams DR, et al.
Tetrahedron Letters, 29(40) (1988)
Preparation of disulfides by the oxidation of thiols using bromine
Wu Xiaoming, et al.
Synthetic Communications, 26(1) (1996)
Bromine
Goehring RR
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)

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