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703540

Sigma-Aldrich

2,2,6,6-Tetramethylpiperidinylmagnesium chloride lithium chloride complex solution

1.0 M in THF/toluene

Synonym(s):

TMPMgCl·LiCl

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$197.00
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$275.00
500 ML
$709.00

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100 ML
$197.00
4 X 25 ML
$275.00
500 ML
$709.00

About This Item

Empirical Formula (Hill Notation):
C9H18Cl2LiMgN
CAS Number:
898838-07-8
Molecular Weight:
242.40
MDL number:
MFCD12546030
UNSPSC Code:
12352103
PubChem Substance ID:
329762048
NACRES:
NA.22

$197.00

Please contact Customer Service for Availability
Request a Bulk Order

form

liquid

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF/toluene
20 % (w/w)

density

0.96 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[Li+].[Cl-].CC1(C)CCCC(C)(C)N1[Mg]Cl

InChI

1S/C9H18N.2ClH.Li.Mg/c1-8(2)6-5-7-9(3,4)10-8;;;;/h5-7H2,1-4H3;2*1H;;/q-1;;;+1;+2/p-2

InChI key

JHBZAAACZVPPRQ-UHFFFAOYSA-L

Application

Selective Deprotonations using Knochel-Hauser-Base
2,2,6,6-Tetramethylpiperidinylmagnesium chloride lithium chloride complex is a non-nucleophilic Knochel-Hauser base[1] mainly used for the magnesiation of functionalized arenes and heteroarenes to prepare the corresponding Grignard reagents.[2][3][4] It can also be used as a base in the synthesis of Π-conjugated polymers via catalyst-transfer polycondensation.[5][6]

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

Product of Albemarle US Inc
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

5.0 °F

Flash Point(C)

-15 °C

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP2181
SHBN9202
SHBM6948
SHBL7221
SHBL3467

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Articles

Selective Metalation and Additions

Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

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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