400173
Lithium tert-butoxide
97%
Synonym(s):
LiOtBu
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About This Item
Linear Formula:
(CH3)3COLi
CAS Number:
Molecular Weight:
80.05
UNSPSC Code:
12352300
NACRES:
NA.22
PubChem Substance ID:
EC Number:
217-611-5
Beilstein/REAXYS Number:
3620018
MDL number:
Assay:
97%
Form:
powder and chunks
InChI key
LZWQNOHZMQIFBX-UHFFFAOYSA-N
InChI
1S/C4H9O.Li/c1-4(2,3)5;/h1-3H3;/q-1;+1
SMILES string
[Li+].CC(C)(C)[O-]
assay
97%
form
powder and chunks
bp
110 °C/at 0.1333 hPa
density
0,897 g/cm3
Quality Level
Application
Lithium tert-butoxide (LiOtBu) is a weakly basic and nucleophilic alkali metal oxide commonly used as an initiator for anionic polymerization.
Other synthetic applications:
Other synthetic applications:
- In combination with potassium diisopropylamide, LiOtBu can be used to deprotonate 1-(phenylseleno) alkenes and bis (phenylseleno) acetals.
- LiOtBu can mediate the α-alkylation reaction of ketones with primary alcohols in the absence of any transition metal catalyst.
- LiOtBu is an effective base for the synthesis of 3,4,5-trisubstituted 3H-oxazol-2-ones and 3,4-disubstituted (Z)-oxazolidin-2-ones from substituted propargyl alcohols and aryl/alkyl isocyanates using DMF as a solvent.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Self-heat. 1 - Skin Corr. 1B
supp_hazards
Storage Class
4.2 - Pyrophoric and self-heating hazardous materials
wgk
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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LiOtBu Promoted 5?Exo?dig Cyclization of Propargyl Alcohols and Isocyanates for the Synthesis of Multisubstituted 3H?Oxazol?2?ones and Oxazolidin?2?ones.
Savarimuthu S A, et al.
ChemistrySelect, 1(9), 2035-2039 (2016)
The role of association/complexation equilibria in the anionic polymerization of (meth) acrylates.
Kunkel D, et al.
Macromolecular Symposia, 60(1), 315-326 (1992)
Lithium tert-Butoxide.
Caine D.
e-EROS Encyclopedia of Reagents for Organic Synthesis. null
Organoselenium chemistry. 4. Deprotonations with potassium diisopropylamide-lithium tert-butoxide. Alkylation of 1-(phenylseleno) alkenes and bis (phenylseleno) acetals.
Raucher S and Koolpe G A
The Journal of Organic Chemistry, 43(19), 3794-3796 (1978)
Lithium tert-butoxide mediated α-alkylation of ketones with primary alcohols under transition-metal-free conditions.
Liang Y F, et al.
Royal Society of Chemistry Advances, 3(21), 7739-7742 (2013)
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