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D40752

Sigma-Aldrich

1,2-Dibromoethane

98%

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:
24893813
NACRES:
NA.22

vapor density

~6.5 (vs air)

Quality Level

200

vapor pressure

11.7 mmHg ( 25 °C)

assay

98%

form

liquid

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.

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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