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Merck
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문서

577928

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution

1 M in toluene

동의어(들):

LiHMDS, Hexamethyldisilazane lithium salt

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About This Item

Linear Formula:
[(CH3)3Si]2NLi
CAS Number:
Molecular Weight:
167.33
Beilstein:
3567910
MDL number:
UNSPSC 코드:
12352111
PubChem Substance ID:
NACRES:
NA.22

농도

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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일반 설명

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

애플리케이션

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.

신호어

Danger

유해 및 위험 성명서

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

표적 기관

Central nervous system

보충제 위험성

Storage Class Code

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

개인 보호 장비

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


시험 성적서(COA)

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Selective fluoroalkylation of organic compounds by tackling the ?negative fluorine effect?
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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)
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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