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Sigma-Aldrich

Lithium bis(trimethylsilyl)amide

97%

Synonym(s):

Hexamethyldisilazane lithium salt

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10 G
€93.30
50 G
€127.00
250 G
€376.00

About This Item

Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
4039-32-1
Molecular Weight:
167.33
EC Number:
223-725-6
MDL number:
MFCD00008261
UNSPSC Code:
12352111
PubChem Substance ID:
24859455
NACRES:
NA.22

€93.30

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Quality Level

200

Assay

97%

form

solid

pH

(12.4 at 23,7 °C)

bp

110-115 °C (at 1.33 hPa)

mp

70-71 °C

density

0.860 g/mL at 25 °C (lit.)

SMILES string

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

InChI

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

InChI key

YNESATAKKCNGOF-UHFFFAOYSA-N

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General description

Lithium bis(trimethylsilyl)amide is a non-nucleophilic strong Brønsted base, which is generally soluble in most of the nonpolar organic solvents. It is most commonly employed in organic reactions.[1][2]

Application

Base employed in generating enolates for the preparation of lactone precursors,[3] pyranones,[4] and cyclohexanes.[5]
Used to catalyze the addition of phosphine P-H bonds to carbodiimides leading to phosphaguanidines.[6] Also used in a novel three-step synthesis of disubstituted 1,2,5-thiadiazoles.[7]

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H228,H251,H314

Hazard Classifications

Eye Dam. 1 - Flam. Sol. 1 - Self-heat. 1 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 2

Flash Point(F)

62.6 °F - closed cup

Flash Point(C)

17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR6417
SHBR6416
SHBR4328
SHBR5680
SHBS0691

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Tetrahedron, 50, 9061-9061 (1994)
Ana I Ojeda-Amador et al.
Inorganic chemistry, 55(11), 5719-5728 (2016-05-14)
Reacting cesium fluoride with an equimolar n-hexane solution of lithium bis(trimethylsilyl)amide (LiHMDS) allows the isolation of CsHMDS (1) in 80% yield (after sublimation). This preparative route to 1 negates the need for pyrophoric Cs metal or organocesium reagents in its
Tetrahedron Letters, 47, 8285-8285 (2006)
Lithium Bis(trimethylsilyl)amide and Tris(trimethylsilyl)amine
Inorganic Syntheses (1966)
Synlett, 507-507 (1993)
View All Related Papers

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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