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400173

Sigma-Aldrich

Lithium tert-butoxide

97%

Synonym(s):

LiOtBu

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About This Item

Linear Formula:
(CH3)3COLi
CAS Number:
1907-33-1
Molecular Weight:
80.05
Beilstein/REAXYS Number:
3620018
EC Number:
217-611-5
MDL number:
MFCD00050479
UNSPSC Code:
12352300
PubChem Substance ID:
24864902
NACRES:
NA.22

Quality Level

200

assay

97%

form

powder and chunks

SMILES string

[Li+].CC(C)(C)[O-]

InChI

1S/C4H9O.Li/c1-4(2,3)5;/h1-3H3;/q-1;+1

InChI key

LZWQNOHZMQIFBX-UHFFFAOYSA-N

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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:
  • 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.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Self-heat. 1 - Skin Corr. 1B

supp_hazards

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

ppe

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

Certificates of Analysis (COA)

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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)
Microstructure analysis of poly (lactic acid) obtained by lithium tert-butoxide as initiator.
Kasperczyk J E, et al.
Macromolecules, 28(11), 3937-3939 (1995)
The role of association/complexation equilibria in the anionic polymerization of (meth) acrylates.
Kunkel D, et al.
Macromolecular Symposia, 60(1), 315-326 (1992)
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)
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