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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
UNSPSC Code:
12352300
NACRES:
NA.22
PubChem Substance ID:
24864902
EC Number:
217-611-5
Beilstein/REAXYS Number:
3620018
MDL number:
MFCD00050479
Assay:
97%
Form:
powder and chunks
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Quality Level

200

assay

97%

form

powder and chunks

bp

110  °C/at 0.1333 hPa

density

0,897 g/cm3

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

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.

signalword

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

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS4329
SHBS3995
SHBR7431
SHBQ3306
SHBK4610

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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)
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)
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