Ethylmagnesium bromide Chemical Properties

Melting point:

-116.3°C

Boiling point:

34.6°C

Density 

1.02 g/mL at 25 °C

Flash point:

<−30 °F

storage temp. 

water-free area

solubility 

Miscible in alcohols, ketones, esters, ethers, hydrocarbons.

form 

Solution

color 

Pale yellow to brown

Water Solubility 

Reacts with water.

Sensitive 

Air & Moisture Sensitive

BRN 

3587203

Exposure limits

ACGIH: TWA 400 ppm; STEL 500 ppm
OSHA: TWA 400 ppm(1200 mg/m3)
NIOSH: IDLH 1900 ppm

InChI

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

InChIKey

TWTWFMUQSOFTRN-UHFFFAOYSA-M

SMILES

C(C)[Mg]Br

CAS DataBase Reference

925-90-6(CAS DataBase Reference)

EPA Substance Registry System

Magnesium, bromoethyl- (925-90-6)

Safety Information

Hazard Codes 

F+,C,F

Risk Statements 

12-14/15-19-22-34-66-67-40-11-14-37

Safety Statements 

16-26-36/37/39-43-45-7/8-27-9

RIDADR 

UN 3399 4.3/PG 1

WGK Germany 

1

F 

1-3-10

TSCA 

Yes

HazardClass 

4.3

PackingGroup 

I

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethylmagnesium bromide Usage And Synthesis

Chemical Properties

Ethylmagnesium bromide is generally sold as a dark brown solution and can be dissolved in diethyl ether, butyl ether, isopropyl ether, THF and anisole.

Uses

Ethylmagnesium Bromide is a useful reagent in preparation of zirconium complexes having two phenoxy-imine chelate ligands for olefin polymerization.

Preparation

Ethylmagnesium bromide is commercially available, usually as a solution in diethyl ether or tetrahydrofuran. It may be prepared in the normal manner of Grignard reagents — by reacting bromoethane with magnesium in diethyl ether:
EtBr + Mg → EtMgBr

Reactions

Ethylmagnesium bromide reacts with water to produce ethane.
CH3CH2MgBr+H2O→CH3-CH3+Mg(OH)Br
Reaction of ethylmagnesium bromide with ethyl acetate in the presence of styrene and titanium(IV) isopropoxide as a catalyst leads to (Z)-1-methyl-2-phenylcyclopropanol in 42% yield.

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. Ethylmagnesium bromide solution (3.0 M in diethyl ether) can be used for copper(I)-catalyzed allylic substitution reaction.
Grignard reagents are organometallic compounds discovered by a French chemist, Victor Grignard in 1900. These compounds can be obtained as a formula “RMgX” by the reaction of halogenated hydrocarbons with magnesium metal in anhydrous solvents such as diethyl ether,1) and have been widely used in organic synthesis.

Hazard

Flammable, dangerous fire risk.

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