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189898

Sigma-Aldrich

Methylmagnesium bromide solution

3.0 M in diethyl ether

Sinónimos:

Bromomethylmagnesium

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About This Item

Fórmula lineal:
CH3MgBr
Número de CAS:
75-16-1
Peso molecular:
119.24
Beilstein/REAXYS Number:
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

signalword

Danger

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

supp_hazards

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

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Certificados de análisis (COA)

Lot/Batch Number
SHBN4763
SHBM8188
SHBM8112
SHBM0873
SHBL3954

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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

Artículos

Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used alkylating and acylating reagents.

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