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Merck
CN

189898

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
UNSPSC Code:
12352111
NACRES:
NA.22
PubChem Substance ID:
24851403
MDL number:
MFCD00000041
Beilstein/REAXYS Number:
3535220

Key Documents

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Product Name

Methylmagnesium bromide solution, 3.0 M in diethyl ether

InChI

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

SMILES string

C[Mg]Br

InChI key

AVFUHBJCUUTGCD-UHFFFAOYSA-M

Quality Level

200

form

liquid

reaction suitability

reaction type: Grignard Reaction

concentration

3.0 M in diethyl ether

density

1.035 g/mL at 25 °C

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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)

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.

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
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Legal Information

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

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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

WGK 1

flash_point_f

-40.0 °F - closed cup

flash_point_c

-40 °C - closed cup

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS8073
SHBR8069
SHBQ4560
SHBP5436
SHBN4763

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Non-solvent post-modifications with volatile reagents for remarkably porous ketone functionalized polymers of intrinsic microporosity
Sirinapa W,et al.
Nature Communications, 14, 2096-2096 (2023)
Asymmetric synthesis of (2R, 3S) and (2S, 3R) precursors of ?-methyl-histidine,-phenylalanine and-tyrosine.
Li G
Tetrahedron Asymmetry, 4(11), 2315-2318 (1993)
Mechanistic insights on the stereoselective nucleophilic 1, 2-addition to sulfinyl imines
Martin H,et al.
The Journal of Organic Chemistry, 79, 2514-2521 (2014)
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)
Organometallic Complexes of Bulky, Optically Active, C 3-Symmetric Tris (4 S-isopropyl-5, 5-dimethyl-2-oxazolinyl) phenylborate (ToP*)
Songchen X,et al.
Organometallics, 34, 3508-3519 (2015)
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