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Sigma-Aldrich

Lithium amide

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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

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Design for Energy Efficiency
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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

Signal Word

Danger

Hazard Statements

H261,H314

Hazard Classifications

Skin Corr. 1B - Water-react 2

Supplementary Hazards

EUH014,EUH029

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
N. Ogawa and Y. Kobayashi,
Tetrahedron Letters, 52, 3001-3004 (2011)
G. Bordeau, et al.,
Tetrahedron Letters, 51, 4429-4432 (2010)
R. Kuwano, et al.,
Synlett, 12, 1819-1824 (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
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