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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


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

189898-4X10ML:
189898-PZ:
189898-VAR:
189898-8L:4548173112022
189898-4X25ML:4548173309088
189898-18L:4548173112008
189898-50ML:4548173292700
189898-20L:
189898-18L-KL:
189898-100ML:4548173111995
189898-BULK:
189898-800ML:4548173112015
189898-18L-C:
189898-4X100ML:4548173341484


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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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)
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Organometallic Complexes of Bulky, Optically Active, C 3-Symmetric Tris (4 S-isopropyl-5, 5-dimethyl-2-oxazolinyl) phenylborate (ToP*)
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Organometallics, 34, 3508-3519 (2015)

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