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Sigma-Aldrich

Lithium amide

greener alternative

powder, 95%

Synonym(s):

Aminolithium, Lithamide

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About This Item

Linear Formula:
LiNH2
CAS Number:
7782-89-0
Molecular Weight:
22.96
EC Number:
231-968-4
MDL number:
MFCD00011093
UNSPSC Code:
12352301
PubChem Substance ID:
24852671
NACRES:
NA.22

assay

95%

form

powder

greener alternative product characteristics

Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

sustainability

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mp

380-400 °C

density

1.178 g/mL at 25 °C (lit.)

greener alternative category

Enabling,

SMILES string

[Li].CN

InChI

1S/Li.H2N/h;1H2/q+1;-1

InChI key

AFRJJFRNGGLMDW-UHFFFAOYSA-N

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General description

Lithium amide (LiNH2) is an amide of an alkali metal with lithium atoms having larger positive charges than hydrogen atoms. It is a moisture-sensitive molecule that converts to LiOH and NH3 on reaction with H2O. LiNH2 is majorly used in hydrogen storage applications.
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Application

Reagent for synthesis of:
Antiinflamatory and preoresolving protectin D1
Chemotype dipeptidyl peptidase IV inhibitors
Sterically congested triarylamines
Dyes displaying large Stokes shifts
GM1 ganglioside derivatives

Reagent for cross-coupling of aryl chlorides and amines

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

hcodes

H261,H314

Hazard Classifications

Skin Corr. 1B - Water-react 2

supp_hazards

EUH014,EUH029

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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G. Bordeau, et al.,
Tetrahedron Letters, 51, 4429-4432 (2010)
Rylan J Lundgren et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(6), 1983-1991 (2009-12-22)
The syntheses of 2-(di-tert-butylphosphino)-N,N-dimethylaniline (L1, 71%) and 2-(di-1-adamantylphosphino)-N,N-dimethylaniline (L2, 74 %), and their application in Buchwald-Hartwig amination, are reported. In combination with [Pd(allyl)Cl](2) or [Pd(cinnamyl)Cl](2), these structurally simple and air-stable P,N ligands enable the cross-coupling of aryl and heteroaryl chlorides
N. Ogawa and Y. Kobayashi,
Tetrahedron Letters, 52, 3001-3004 (2011)
R. Kuwano, et al.,
Synlett, 12, 1819-1824 (2010)
Yukihiro Nishio et al.
Bioorganic & medicinal chemistry letters, 20(24), 7246-7249 (2010-11-16)
Structures containing the (R)-3-amino-3-methyl piperidine unit as a new pharmacophore moiety have been shown to possess moderate inhibitory activity for DPP-4 with good pharmacokinetics profile. One of these compounds was found to have good oral bioavailability and PK/PD profile in
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