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240656

Sigma-Aldrich

1,2-Dibromoethane

≥99%

Synonym(s):
Ethylene dibromide, EDB
Linear Formula:
BrCH2CH2Br
CAS Number:
Molecular Weight:
187.86
Beilstein:
605266
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor density

~6.5 (vs air)

vapor pressure

11.7 mmHg ( 25 °C)

assay

≥99%

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.

Packaging

5, 100 g in glass bottle

Other Notes

May darken in storage

Signal Word

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 Code

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

1, 2-Dibromoethane
Maynard GD
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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.
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)
A four-component reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, 1,2-dibromoethane, and hydrazines
Zheng D, et al.
Organic & Biomolecular Chemistry, 13(41), 10370-10375 (2015)

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