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Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution

1 M in toluene

Synonym(s):

LiHMDS, Hexamethyldisilazane lithium salt

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100 ML
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About This Item

Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
4039-32-1
Molecular Weight:
167.33
Beilstein/REAXYS Number:
3567910
MDL number:
MFCD00008261
UNSPSC Code:
12352111
PubChem Substance ID:
24880899
NACRES:
NA.22

$74.60

Available to ship onApril 24, 2025Details

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Quality Level

200

concentration

1 M in toluene

density

0.860 g/mL at 25 °C

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 solution (LiHMDS) is generally used in organic synthesis as a non-nucleophilic strong Bronsted base.[1]

application

LiHMDS can be used as a reagent:
  • In the deprotonation and nucleophilic difluoromethylation reactions.[2][3]
  • To synthesize isoquinoline derivatives by the addition of N-iodosuccinimide (NIS) to the α-benzyl tosylmethyl isocyanides.[4]
  • To prepare arylboronic acid pinacol esters by the reaction of aryl fluorides with bis(pinacolato)diboron via palladium-catalyzed cross-coupling reaction.[5]

Lithium bis(trimethylsilyl)amide is generally used in organic synthesis as a non-nucleophilic strong Brønsted base. It can be used for salt metathesis reaction for the synthesis of cesium bis(trimethylsilyl)amide (CsHMDS) and lithium fluoride by reacting with cesium fluoride.[6]

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Self-heat. 1 - Skin Corr. 1B - STOT RE 2 - STOT SE 3

target_organs

Central nervous system

supp_hazards

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

48.0 °F - closed cup

flash_point_c

8.9 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP9616
SHBP9615
SHBM8890
SHBL9620
SHBL3411

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Structural Studies of Cesium, Lithium/Cesium, and Sodium/Cesium Bis (trimethylsilyl) amide (HMDS) Complexes
Ojeda-Amador AI, et al.
Inorganic Chemistry, 55(11), 5719-5728 (2016)
Synthesis of 1-Substituted Isoquinolines by Heterocyclization of TosMIC Derivatives: Total Synthesis of Cassiarin A
Gutierrez S, et al.
Organic Letters, 38(18), 187-208 (2016)
LiHMDS-Promoted Palladium or Iron-Catalyzed ipso-Defluoroborylation of Aryl Fluorides
Zhao X, et al.
Organic Letters, 38(18), 25-44 (2011)
Selective fluoroalkylation of organic compounds by tackling the ?negative fluorine effect?
Fluorous chemistry, 38(18), 187-208 (2016)
Development of synthetic routes to dolutegravir
Syntheses of Heterocyclic Compounds Synthesis of Heterocycles in Contemporary Medicinal Chemistry, 38(18), 3187-3188 (1997)
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Questions

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  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?

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    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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