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Isopropylmagnesium chloride solution

2.0 M in THF

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Synonym(s):
Chloro 1-methylethyl magnesium, Chloroisopropylmagnesium, Isopropylmagnesium chloride, iPrMgCl
Linear Formula:
(CH3)2CHMgCl
CAS Number:
Molecular Weight:
102.85
Beilstein:
4124221
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

reaction suitability

reaction type: Grignard Reaction

concentration

2.0 M in THF

density

0.975 g/mL at 25 °C

SMILES string

CC(C)[Mg]Cl

InChI

1S/C3H7.ClH.Mg/c1-3-2;;/h3H,1-2H3;1H;/q;;+1/p-1

InChI key

GPIBKUJXKCEZOH-UHFFFAOYSA-M

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1 of 4

This Item
224383224405256021
density

0.975 g/mL at 25 °C

density

0.834 g/mL at 25 °C

density

0.878 g/mL at 25 °C

density

0.777 g/mL at 25 °C

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

concentration

2.0 M in THF

concentration

2.0 M in diethyl ether

concentration

2.0 M in diethyl ether

concentration

1.0 M in diethyl ether

General description

Isopropylmagnesium chloride is a highly reactive organomagnesium halide formed by the reaction of magnesium metal with isopropyl chloride. It is used in the Grignard reaction to form new carbon-carbon bonds.

Application

Isopropylmagnesium chloride solution (2.0 M in THF) can be used as a reagent to synthesize:      
  • 2,6-Diiodobenzaldehyde derivatives via regioselective metal-iodine exchange of 5-substituted 1,2,3-triiodobenzene in the presence of ethyl formate as a formylating agent.      
  • Arene and heteroarene sulfonamides from aryl and heteroaryl bromides via the formation of corresponding Grignard reagents.
  • Symmetrical pyridyl monoselenides by treating with bromo/iodopyridines followed by quenching with selenyl chloride, SeCl2.

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 - Water-react 1

Supplementary Hazards

Storage Class Code

4.3 - Hazardous materials, which set free flammable gases upon contact with water

WGK

WGK 1

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup


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Oleg V Larionov et al.
Organic letters, 16(3), 864-867 (2014-01-15)
A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method

Articles

Substantial progress has been made in magnesium–halogen exchange reactions used for the preparation of functionalized Grignard reagents containing sensitive moieties such as ester or cyano groups.

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