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Merck
CN

345113

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
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24861295
MDL number:
MFCD00015225
Beilstein/REAXYS Number:
3535184

Key Documents

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InChI

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

SMILES string

CCCC[Mg]CCCC

InChI key

ODHFJIDDBSDWNU-UHFFFAOYSA-N

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in heptane

density

0.713 g/mL at 25 °C

Quality Level

100

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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.

Other Notes

  • Contains up to 1 Wt% Triethylaluminum as a Viscosity Reducer
  • This material can vary from light to very dark in appearance. These differences in color will have no effect on use.
  • May contain up to 3% THF

signalword

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

supp_hazards

EUH014

Storage Class

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

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBS4899
SHBR8668
SHBQ7951
SHBP3477
SHBN9190

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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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