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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:
Molecular Weight:
119.24
Beilstein:
3535220
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.

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

Central nervous 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


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Asymmetric synthesis of (2R, 3S) and (2S, 3R) precursors of ?-methyl-histidine,-phenylalanine and-tyrosine.
Li G
Tetrahedron Asymmetry, 4(11), 2315-2318 (1993)
Diastereoselective preparation of cyclic ?-aminoketals. Application to the total synthesis of piperidine alkaloids
Al-Sarabi AE
ARKIVOC (Gainesville, FL, United States), 1, 119-133 (2007)
Snahel Patel et al.
Journal of medicinal chemistry, 58(1), 401-418 (2014-10-24)
Dual leucine zipper kinase (DLK, MAP3K12) was recently identified as an essential regulator of neuronal degeneration in multiple contexts. Here we describe the generation of potent and selective DLK inhibitors starting from a high-throughput screening hit. Using proposed hinge-binding interactions

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