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8.18287

Sigma-Aldrich

Lithium iodide

anhydrous for synthesis

Synonym(s):

Lithium iodide

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About This Item

Empirical Formula (Hill Notation):
ILi
CAS Number:
10377-51-2
Molecular Weight:
133.85
MDL number:
MFCD00011092
UNSPSC Code:
12352302
EC Index Number:
233-822-5
NACRES:
NA.22
form:
powder
solubility:
soluble 1640 g/L
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Quality Level

200

form

powder

mp

450 °C

solubility

soluble 1640 g/L

density

4 g/cm3 at 20 °C

bulk density

1000 kg/m3

storage temp.

2-30°C

SMILES string

[Li+].[I-]

InChI

1S/HI.Li/h1H;/q;+1/p-1

InChI key

HSZCZNFXUDYRKD-UHFFFAOYSA-M

Application

Lithium iodide (LiI) can be used as a catalyst to synthesize:
  • N-alkyl 2-pyridone derivatives via O- to N-[1,3]-alkyl migration.[1]
  • β-mannosides and β-rhamnosides from glycosyl hemiacetals via one-pot chlorination, iodination, and glycosylation reaction.[2]

It can also be used as:
  • Solid electrolyte in the synthesis of Vycor glass/LiI composites applicable in the development of solid-state batteries.[3]
  • Iodine source to synthesize primary, secondary, and bridgehead tertiary alkyl iodides by PPh3-catalyzed iododecarboxylation of aliphatic carboxylates.[4]

Analysis Note

Assay (argentometric): ≥ 98.0 %
Water (K. F.): ≤ 0.50 %

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Preparation of N-alkyl 2-pyridones via a lithium iodide promoted O- to N-alkyl migration: scope and mechanism
Sarah Z Tasker, et al.
The Journal of Organic Chemistry, 77(18), 8220-8230 (2012)
Ming-Chen Fu et al.
Organic letters, 22(21), 8572-8577 (2020-10-23)
Under irradiation of 456 nm blue light-emitting diodes, PPh3 catalyzes the iododecarboxylation of aliphatic carboxylic acid derived N-(acyloxy)phthalimide with lithium iodide as an iodine source. The reaction delivers primary, secondary, and bridgehead tertiary alkyl iodides in acetone solvent, and the
Imlirenla Pongener et al.
Chemical science, 12(29), 10070-10075 (2021-08-12)
Stereoselective β-mannosylation is one of the most challenging problems in the synthesis of oligosaccharides. Herein, a highly selective synthesis of β-mannosides and β-rhamnosides from glycosyl hemi-acetals is reported, following a one-pot chlorination, iodination, glycosylation sequence employing cheap oxalyl chloride, phosphine
Nanostructured ionic conductors: A study of Vycor7930-LiI composites
Albert Stephanie, et al.
Materials Science and Engineering Technology, 150(3), 199-202 (2008)
Sarah Z Tasker et al.
The Journal of organic chemistry, 77(18), 8220-8230 (2012-08-30)
An efficient and inexpensive LiI-promoted O- to N-alkyl migration of 2-benzyloxy-, 2-allyloxy-, and 2-propargyloxypyridines and heterocycles is reported. The reaction produces the corresponding N-alkyl 2-pyridones and analogues under green, solvent-free conditions in good to excellent yields (30 examples, 20-97% yield).

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