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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:
676-58-4
Molecular Weight:
74.79
Beilstein:
3587199
MDL number:
MFCD00000468
UNSPSC Code:
12352103
PubChem Substance ID:
24851404
NACRES:
NA.22

autoignition temp.

609 °F

Quality Level

200

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.
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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

EUH014,EUH019

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

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  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. Is the BHT inhibitor present in Product 189901, Methylmagnesium chloride solution?

    Yes, BHT is present in the THF. This information can be found on the MSDS, which is available from our website.

  6. Can Product 189901, Methylmagnesium chloride solution, be used if a precipitate is present?

    If a precipitate is present, the product can be heated and stirred until the precipitate is dissolved.

  7. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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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