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189901

Sigma-Aldrich

Methylmagnesium chloride solution

3.0 M in THF

Synonym(s):

Chloromethylmagnesium, Methyl magnesium chloride, Methylmagnesiumchloride

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About This Item

Linear Formula:
CH3MgCl
CAS Number:
Molecular Weight:
74.79
Beilstein:
3587199
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

autoignition temp.

609 °F

Quality Level

reaction suitability

reaction type: Grignard Reaction

concentration

3.0 M in THF

density

1.013 g/mL at 25 °C

SMILES string

C[Mg]Cl

InChI

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

InChI key

RQNMYNYHBQQZSP-UHFFFAOYSA-M

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Application

Methylmagnesium chloride solution (3 M in THF) undergoes 1,3-addition with dialdose derived nitrones to form N-benzylhydroxylamines. The reductive cleavage of the N-O bond of these N-benzylhydroxylamines results in N-benzylaminosugars, which are key moieties of bioactive compounds. It can also react with Garner type aldehydes to form the corresponding secondary alcohols.

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 Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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A new route to aminosugars from sugar nitrones: synthesis of 6-deoxynojirimycin.
Dhavale DD
Tetrahedron Asymmetry, 8(9), 1475-1486 (1997)

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