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230111

Sigma-Aldrich

Isopropylmagnesium chloride solution

2.0 M in THF

Synonym(s):

Chloro 1-methylethyl magnesium, Chloroisopropylmagnesium, Isopropylmagnesium chloride, iPrMgCl

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About This Item

Linear Formula:
(CH3)2CHMgCl
CAS Number:
1068-55-9
Molecular Weight:
102.85
Beilstein:
4124221
MDL number:
MFCD00000466
UNSPSC Code:
12352103
PubChem Substance ID:
24853775
NACRES:
NA.22

Quality Level

200

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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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

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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

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

Certificates of Analysis (COA)

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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

Mild Mg – Halogen Exchange

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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