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D40752

Sigma-Aldrich

1,2-Dibromoethane

98%

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

98%

refractive index

n20/D 1.539 (lit.)

bp

131-132 °C (lit.)

mp

8-11 °C (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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Application

1,2-Dibromoethane can be used:
  • To prepare functionalized styrenes by reacting with arylboronic acids via palladium-catalyzed cross-coupling reaction.
  • Along with potassium iodide(KI) for α-acyloxylation of ketones with carboxylic acids without the use of transition metals and strong oxidants.
  • In the synthesis of 5-aryl/alkyl-2-vinyl-2H-tetrazoles through one-pot regioselective vinylation of 5-tetrazoles without a metal catalyst or organocatalyst.
  • In the preparation of aryltriethoxysilane using aryl bromide, Mg powder and tetraethyl orthosilicate through sonochemical Barbier-type reaction.
  • As a reoxidizing reagent along with a silver catalyst in the regioselective carbomagnesiation of terminal alkynes with alkyl Grignard reagents.

Packaging

1 kg in glass bottle
5, 250 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 and KI mediated α-acyloxylation of ketones with carboxylic acids
Wang X, et al.
Chinese Chemical Letters = Zhongguo Hua Xue Kuai Bao, 5(16), 2891-2894 (2019)
One-pot regioselective vinylation of tetrazoles: preparation of 5-substituted 2-vinyl-2H-tetrazoles
Roh J, et al.
Tetrahedron Letters, 51(10), 1411-1414 (2010)
Silver-catalyzed carbomagnesiation of terminal aryl and silyl alkynes and enynes in the presence of 1, 2-dibromoethane
Fujii Y, et al.
Chemical Communications (Cambridge, England), 47(9), 1115-1117 (2009)
A facile and efficient synthesis of aryltriethoxysilanes via sonochemical Barbier-type reaction
Lee AS, et al.
Tetrahedron Letters, 47(39), 7085-7087 (2006)
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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