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345113

Sigma-Aldrich

Di-n-butylmagnesium solution

Di-n-butylmagnesium solution

1.0 M in heptane

Synonym(s):

Bis-n-butylmagnesium, Dibutylmagnesium

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About This Item

Linear Formula:
[CH3(CH2)3]2Mg
CAS Number:
1191-47-5
Molecular Weight:
138.53
Beilstein:
3535184
MDL number:
MFCD00015225
UNSPSC Code:
12352103
PubChem Substance ID:
24861295
NACRES:
NA.22
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reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in heptane

density

0.713 g/mL at 25 °C

SMILES string

CCCC[Mg]CCCC

InChI

1S/2C4H9.Mg/c2*1-3-4-2;/h2*1,3-4H2,2H3;

InChI key

ODHFJIDDBSDWNU-UHFFFAOYSA-N

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General description

Di-n-butylmagnesium solution is a useful reagent for the synthesis of organomagnesium compounds.

Application

Di-n-butylmagnesium solution can be used as a reagent for the deprotection of aromatic and aliphatic benzyl thioethers to synthesize corresponding benzylthiols in the presence of titanocene dichloride[1]. It can also be used as a catalyst to synthesize enantioenriched nitrogen-containing heterocyclic derivatives by the asymmetric ring-opening reaction of aziridines with substituted tetrazoles in the presence of chiral ligand[2].

Signal Word

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Target Organs

Central nervous system

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 2

Flash Point(F)

21.2 °F - closed cup

Flash Point(C)

-6 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS4899
SHBR8668
SHBQ7951
SHBP3477
SHBN9190

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Dan Li et al.
Organic letters, 19(12), 3211-3214 (2017-05-31)
A magnesium-catalyzed asymmetric ring-opening reaction of aziridines with substituted tetrazoles is reported. The current protocol proceeds smoothly and gives the corresponding desymmetrization products in high yields and good enantioselectivities. A new chiral ligand was synthesized from azetidine and (R)-BINOL and
A mild and practical deprotection method for benzyl thioethers
Akao A, et al.
Tetrahedron Letters, 47, 5337-5340 (2006)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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Reviews

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  1. Antarctica
    • Review 1
    • Votes 14
    1 out of 5 stars.

    Terrible product - consistently contaminated with THF

    Contains THF, should be advertised as Mg(nBu)2(THF)2 for clarity.

    Helpful?

    1. Response from MilliporeSigma:

      Thank you for your review. We are sorry to hear that your experience did not match your product expectations.

      Based on the Certificate of Analysis, this product "may contain up to 3% THF based on information from the vendor/QC". Please refer to the sample COA in the Documentation section: https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/345113-BULKSHBQ7951.pdf

      We encourage customers who experience problems with our products to call or email us for additional technical support. Please visit https://www.sigmaaldrich.com/US/en/support/customer-support to submit a Product Technical Inquiry.

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