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345113

Sigma-Aldrich

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

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. 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.

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

Certificates of Analysis (COA)

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A mild and practical deprotection method for benzyl thioethers
Akao A, et al.
Tetrahedron Letters, 47, 5337-5340 (2006)
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

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