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225770

Lithium bis(trimethylsilyl)amide solution

1.0 M in THF

Lithium bis(trimethylsilyl)amide solution

Synonym(s):

Hexamethyldisilazane lithium salt

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2 X 2 ML

$16.20

4 X 25 ML

$79.20

100 ML

$84.90

4 X 100 ML

$224.00

800 ML

$369.00

1 L

$389.00

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$1,750.00

18 L

$3,090.00

$16.20

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About This Item

Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
Molecular Weight:
167.33
UNSPSC Code:
12352111
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3567910
Concentration:
1.0 M in THF
Form:
liquid

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InChI

1S/C6H18NSi2.Li/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1

SMILES string

[Li]N([Si](C)(C)C)[Si](C)(C)C

InChI key

YNESATAKKCNGOF-UHFFFAOYSA-N

form

liquid

concentration

1.0 M in THF

density

0.891 g/mL at 25 °C

Quality Level

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This Item
766917577928324620
concentration

1.0 M in THF

concentration

1.5 M in THF

concentration

1 M in toluene

concentration

-

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

200

form

liquid

form

liquid

form

-

form

solid

density

0.891 g/mL at 25 °C

density

0.893 g/mL at 25 °C

density

0.860 g/mL at 25 °C

density

0.860 g/mL at 25 °C (lit.)

General description

Lithium bis(trimethylsilyl)amide (LHMDS) is a non-nucleophilic strong base widely used in organic synthesis for deprotonation reactions and base-catalyzed reactions. It is generally soluble in most nonpolar organic solvents.

Application

Lithium bis(trimethylsilyl)amide solution (1.0 M in THF) can be used as a base:
  • To catalyze polymerization reaction in the synthesis of poly(p-benzamide)s.
  • In the synthesis of cyclic poly(α-peptoid)s and α-(difluoromethyl)styrene.
  • In directed aldol condensations and Darzens condensation reactions; α-arylation of aryl ester derivatives and allylic amination reaction.
  • For the generation of kinetic enolates than sodium hexamethyldisilazide (NaHMDS) because the enolates produced are more regiostable than those produced with NaHMDS.

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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Danger

Hazard Classifications

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

target_organs

Central nervous system, Respiratory system

supp_hazards

Storage Class

3 - Flammable liquids

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup


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? -(Difluoromethyl) styrene: improved approach to grams scale synthesis
Justyna WK,et al.
Journal of Fluorine Chemistry, 179, 175-178 (2015)
Macromolecules, 39, 5347-5347 (2006)
Hexamethyldisilazane-mediated controlled polymerization of alpha-amino acid N-carboxyanhydrides.
Hua Lu et al.
Journal of the American Chemical Society, 129(46), 14114-14115 (2007-10-30)
Daniele Fabbri et al.
Environmental science & technology, 42(8), 2957-2963 (2008-05-24)
Using the pyrolysis-gas chromatography-mass spectrometry and off-line pyrolysis/silylation methods for lignites from three Miocene brown coal basins of Poland resulted in the characterization of many organic compounds, including dominant cellulose degradation products such as levoglucosan, 1,6-anhydro-beta-D-glucofuranose, and 1,4:3,6-dianhydroglucopyranose. Levoglucosan is
A Sebok et al.
Journal of chromatography. A, 1211(1-2), 104-112 (2008-10-14)
This paper presents a derivatization, mass fragmentation study relating to the most common six cholic acids, such as cholic, lithocholic, chenodeoxycholic, ursodeoxycholic, 3-hydroxy,7-ketocholanic and dehydrocholic acids, identified and quantified as pollutants in the aquatic environment at the first time. Derivatizations

Questions

1–3 of 3 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/418/501/product-dating-information-06-25-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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  3. Is methanol employed in the production process of the Lithium bis(trimethylsilyl)amide solution, product number 225770?

    1 answer
    1. Methanol is not used in the synthesis of product no. 225770 Lithium bis(trimethylsilyl)amide solution. Methanol residue is highly unlikely to be present.

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