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Merck
CN

577928

Lithium bis(trimethylsilyl)amide solution

1 M in toluene

Synonym(s):

LiHMDS, 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:
24880899
MDL number:
MFCD00008261
Beilstein/REAXYS Number:
3567910

Key Documents

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Product Name

Lithium bis(trimethylsilyl)amide solution, 1 M in toluene

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

concentration

1 M in toluene

density

0.860 g/mL at 25 °C

Quality Level

200

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Application

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

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.

General description

Lithium bis(trimethylsilyl)amide solution (LiHMDS) is generally used in organic synthesis as a non-nucleophilic strong Bronsted base.

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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

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

Regulatory Information

易制毒化学品（3类）
危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBS6675
SHBP9616
SHBP9615
SHBM8890
SHBL9620

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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)
Lithium and potassium bis (trimethylsilyl) amide: Utilizing non-nucleophilic bases as nitrogen sources
Bruning J, et al.
Tetrahedron Letters, 38(18), 3187-3188 (1997)
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