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Sigma-Aldrich

Ethylmagnesium bromide solution

3.0 M in diethyl ether

Synonym(s):

EtMgBr solution

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About This Item

Linear Formula:
CH3CH2MgBr
CAS Number:
925-90-6
Molecular Weight:
133.27
Beilstein/REAXYS Number:
3587203
MDL number:
MFCD00000043
UNSPSC Code:
12352103
PubChem Substance ID:
24851402
NACRES:
NA.22

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

concentration

3.0 M in diethyl ether

density

1.02 g/mL at 25 °C

SMILES string

CC[Mg]Br

InChI

1S/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1

InChI key

TWTWFMUQSOFTRN-UHFFFAOYSA-M

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General description

Ethylmagnesium bromide, an organomagnesium compound, is commonly known as Grignard reagent. It is a powerful carbon nucleophile mainly used for C-C bond formation.

Application

Ethylmagnesium bromide solution (3.0 M in diethyl ether) can be used for copper(I)-catalyzed allylic substitution reaction.

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
View returnable container options.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

target_organs

Respiratory system

supp_hazards

EUH014,EUH019

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 1

flash_point_f

-40.0 °F - closed cup

flash_point_c

-40 °C - closed cup

ppe

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

Certificates of Analysis (COA)

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Enantioselective Copper-Catalyzed SN2? Substitution with Grignard Reagents.
Alexakis A, et al.
Synlett, 0927-0930 (2001)
Organic Chemistry, 542-542 (2008)
Janne E Tønder et al.
Organic & biomolecular chemistry, 2(10), 1447-1455 (2004-05-12)
Copper mediated allylic substitutions and conjugate additions to geranyl, cinnamyl and allylic indole compounds have been investigated with the aim of finding a method for the creation of the all-carbon quaternary centre present in the natural product lyngbyatoxin A. Reaction
R G Xie et al.
Steroids, 55(11), 488-490 (1990-11-01)
The reaction of ethyl magnesium bromide and 17 alpha-ethynylestradiol with formaldehyde in the presence of triethyl phosphate or hexamethylphosphoramide gave the 2- and 4-formyl-17 alpha-ethynylestradiol in high yield. Treatment of the formyl derivatives with an alkaline solution of hydrogen peroxide
T Nishiyama et al.
Chemical & pharmaceutical bulletin, 48(12), 1999-2002 (2001-01-06)
The direct alpha-bromination of various ketones using trifluoromethanesulfonic anhydride and Grignard reagent or magnesium bromide in ether gave the corresponding alpha-bromo ketones in moderate to good yields under mild reaction conditions.
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