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189898

Sigma-Aldrich

Methylmagnesium bromide solution

3.0 M in diethyl ether

Synonym(s):

Bromomethylmagnesium

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About This Item

Linear Formula:
CH3MgBr
CAS Number:
75-16-1
Molecular Weight:
119.24
Beilstein:
3535220
MDL number:
MFCD00000041
UNSPSC Code:
12352111
PubChem Substance ID:
24851403
NACRES:
NA.22

Quality Level

200

reaction suitability

reaction type: Grignard Reaction

concentration

3.0 M in diethyl ether

density

1.035 g/mL at 25 °C

SMILES string

C[Mg]Br

InChI

1S/CH3.BrH.Mg/h1H3;1H;/q;;+1/p-1

InChI key

AVFUHBJCUUTGCD-UHFFFAOYSA-M

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General description

Methylmagnesium bromide solution, also known as bromomethylmagnesium, is both a Lewis acid and nucleophile. It is commonly used as a grignard reagent in organic synthesis reactions.

Application

Methylmagnesium bromide solution (3M in diethyl ether) is used to synthesize:
  • 3S-(Boc-amino)-2,4-dimethyl-2-pentanol and methyl tert-butyl (S)-sulfoxide.
  • Methyl potassium polyimide (K-PIM-1) (MeMgBr).
  • 3(4R)-{3(2R,3S)-[4′-(1′-triphenylmethyl)imidazole]-2-bromo-1-oxobutyl)-4-phenyl2-oxazolidinone
  • Benzyl 2-(2-oxopropyl)piperidine-1-carboxylate
  • (R*, R*) 1-[1-(1-phenylethyl)pyrrolidin-2-yl]propan-2-one)

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

Signal Word

Danger

Hazard Statements

H224,H260,H302,H314,H336

Hazard Classifications

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

Target Organs

Central nervous system

Supplementary Hazards

EUH019

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

Certificates of Analysis (COA)

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Tetrahedron Asymmetry, 4(11), 2315-2318 (1993)
Diastereoselective preparation of cyclic ?-aminoketals. Application to the total synthesis of piperidine alkaloids
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ARKIVOC (Gainesville, FL, United States), 1, 119-133 (2007)
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Journal of medicinal chemistry, 58(1), 401-418 (2014-10-24)
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