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189871

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:
Molecular Weight:
133.27
Beilstein:
3587203
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.

Legal Information

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

Signal Word

Danger

Hazard Statements

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

Supplementary Hazards

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

-40.0 °F - closed cup

Flash Point(C)

-40 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank II
2nd spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

189871-8L:4548173111988
189871-4X25ML:4548173309071
189871-PZ:
189871-18L-C:
189871-VAR:
189871-BULK:
189871-4X10ML:4548173304571
189871-800ML:4548173111971
189871-100ML:4548173111957
189871-18L:4548173111964
189871-20L:


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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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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