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225770

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution

1.0 M in THF

Synonym(s):

Hexamethyldisilazane lithium salt

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About This Item

Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
4039-32-1
Molecular Weight:
167.33
Beilstein:
3567910
MDL number:
MFCD00008261
UNSPSC Code:
12352111
PubChem Substance ID:
24853520
NACRES:
NA.22

form

liquid

Quality Level

200

concentration

1.0 M in THF

density

0.891 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 (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.
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Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

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Description
Pricing

Signal Word

Danger

Hazard Statements

H225,H314,H335,H336,H351

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

225770-18L-KL:
225770-2X2ML:4548173351803
225770-VAR:
225770-200L:4548173119250
225770-20L:
225770-1L:4548173119243
225770-18L-C:
225770-4X25ML:4548173306087
225770-4X10ML:4548173304298
225770-100L:4548173119212
225770-18L:4548173119236
225770-4X100ML:4548173336671
225770-PZ:
225770-8L:4548173119274
225770-800ML:4548173119267
225770-100G:
225770-BULK:
225770-100ML:4548173119229

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ1975
STBK6021
STBK3559
SHBM8360
SHBM8111

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Macromolecules, 39, 5347-5347 (2006)
Nan Li et al.
Lab on a chip, 8(12), 2105-2112 (2008-11-22)
High-density live cell array serves as a valuable tool for the development of high-throughput immunophenotyping systems and cell-based biosensors. In this paper, we have, for the first time, demonstrated a simple fabrication process to form the hexamethyldisilazane (HMDS) and poly(ethylene
Tatsuya Nitabaru et al.
Journal of the American Chemical Society, 131(38), 13860-13869 (2009-09-10)
Full details of an anti-selective catalytic asymmetric nitroaldol reaction promoted by a heterobimetallic catalyst comprised of Nd(5)O(O(i)Pr)(13), an amide-based ligand, and NaHMDS (sodium hexamethyldisilazide) are described. A systematic synthesis and evaluation of amide-based ligands led to the identification of optimum
Juliana Tsz Yan Lee et al.
Scanning, 34(1), 12-25 (2012-04-26)
Common dehydration methods of cells on biomaterials for scanning electron microscopy (SEM) include air drying, hexamethyldisilazane (HMDS) or tetramethysilane (TMS) treatment and critical point drying (CPD). On the other side, freeze-drying has been widely employed in dehydrating biological samples and
Xiaoguang Li et al.
Chemical communications (Cambridge, England), 47(38), 10761-10763 (2011-08-30)
A silica microsphere suspension and a silica sol are employed in a two-step dipping process for the preparation of a superhydrophobic surface. It's not only a facile way to achieve the lotus effect, but can also create a multi-functional surface
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