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240656

Sigma-Aldrich

1,2-Dibromoethane

≥99%

Sinónimos:

EDB, Ethylene dibromide

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About This Item

Fórmula lineal:
BrCH2CH2Br
Número de CAS:
106-93-4
Peso molecular:
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

Certificados de análisis (COA)

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1, 2-dibromoethane-A versatile reagent in organic synthesis
Aluri BR
Synlett, 2008(10), 1579-1580 (2008)
1, 2-Dibromoethane
Maynard GD
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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
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.
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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