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240656

Sigma-Aldrich

1,2-Dibromoethane

≥99%

Synonym(s):

EDB, Ethylene dibromide

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About This Item

Linear Formula:
BrCH2CH2Br
CAS Number:
106-93-4
Molecular Weight:
187.86
Beilstein/REAXYS Number:
605266
EC Number:
203-444-5
MDL number:
MFCD00000233
UNSPSC Code:
12352100
PubChem Substance ID:
24854427
NACRES:
NA.22

vapor density

~6.5 (vs air)

vapor pressure

11.7 mmHg ( 25 °C)

assay

≥99%

form

liquid

refractive index

n20/D 1.539 (lit.)

bp

131-132 °C (lit.)

mp

8-11 °C (lit.)

solubility

water: soluble 250 part
alcohol: miscible(lit.)
diethyl ether: miscible(lit.)

density

2.18 g/mL at 25 °C (lit.)

SMILES string

BrCCBr

InChI

1S/C2H4Br2/c3-1-2-4/h1-2H2

InChI key

PAAZPARNPHGIKF-UHFFFAOYSA-N

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General description

1,2-Dibromoethane (DBE) is an organobromine compound that is used as an ‘entrainment reagent′ to activate magnesium in Grignard reagents. It is also a useful reagent for activating zinc. DBE is used as an intermediate in the synthesis of dyes, pesticides and pharmaceuticals.

Application

1,2-Dibromoethane can be used as a reagent to prepare:
  • Vinyl bromide and 1,2-disubstituted ethane derivatives.
  • Vinyl aromatic compounds by palladium-catalyzed cross-coupling reaction with various arylboronic acids via in situ formation of vinyl bromide.
  • 2-arylsulfonyl hydrazones by reacting with aryldiazonium tetrafluoroborates, sulfur dioxide and hydrazines.

It can also be used as a bromine source in organic synthesis to brominate carbanions.

Other Notes

May darken in storage

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

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1, 2-dibromoethane-A versatile reagent in organic synthesis
Aluri BR
Synlett, 2008(10), 1579-1580 (2008)
Yuuki Fujii et al.
Chemical communications (Cambridge, England), (9)(9), 1115-1117 (2009-02-20)
Regioselective carbomagnesiation of terminal alkynes and enynes with alkyl Grignard reagents has been achieved by the combined use of a silver catalyst and 1,2-dibromoethane.
Maya G Deshmukh et al.
Structure (London, England : 1993), 29(8), 823-833 (2021-06-24)
There is a clinical need for direct-acting antivirals targeting SARS-CoV-2, the coronavirus responsible for the COVID-19 pandemic, to complement current therapeutic strategies. The main protease (Mpro) is an attractive target for antiviral therapy. However, the vast majority of protease inhibitors
1, 2-Dibromoethane
Maynard GD
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Saturation vapor pressures and transition enthalpies of low-volatility organic molecules of atmospheric relevance: from dicarboxylic acids to complex mixtures.
Merete Bilde et al.
Chemical reviews, 115(10), 4115-4156 (2015-05-02)
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