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225770

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
UNSPSC Code:
12352111
NACRES:
NA.22
PubChem Substance ID:
24853520
MDL number:
MFCD00008261
Beilstein/REAXYS Number:
3567910
Concentration:
1.0 M in THF
Form:
liquid
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form

liquid

Quality Segment

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

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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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

EUH014,EUH019

Storage Class

3 - Flammable liquids

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.

Class I Designated Chemical Substances

prtr

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

fsl

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

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

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