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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

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

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.
  • β-mannosides and β-rhamnosides from glycosyl hemiacetals via one-pot chlorination, iodination, and glycosylation reaction.

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

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)

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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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)
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
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
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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