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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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4 X 25 ML
$89.70
100 ML
$90.40
800 ML
$271.00
4 X 100 ML
$295.00
2.5 L
$381.00

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4 X 25 ML
$89.70
100 ML
$90.40
800 ML
$271.00
4 X 100 ML
$295.00
2.5 L
$381.00

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

$89.70

In StockDetails

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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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4542
STBL3895
STBL2629
STBL0774
STBK7590

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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.

Questions

1–2 of 2 Questions  

  1. 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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  2. 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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