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703788

Sigma-Aldrich

Sodium tert-butoxide

99.9%

Synonym(s):

Sodium 2-methylpropan-2-olate, Sodium t-butoxide, Sodium tert-butanolate, Sodium tert-butylate

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About This Item

Linear Formula:
NaOC(CH3)3
CAS Number:
865-48-5
Molecular Weight:
96.10
Beilstein/REAXYS Number:
3654215
EC Number:
212-741-9
MDL number:
MFCD00040575
UNSPSC Code:
12352107
PubChem Substance ID:
329762066
NACRES:
NA.22

assay

99.9%

form

powder

SMILES string

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

InChI

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

InChI key

MFRIHAYPQRLWNB-UHFFFAOYSA-N

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Application

Sodium tert-butoxide can be used as:
  • A promoter for the synthesis of biaryls by C-H bond arylation of aromatic compounds with haloarenes.
  • A base in palladium catalyzed amination reactions.
  • A base in the synthesis of aryl tert-butyl ethers from unactivated aryl halides in presence of palladium catalyst.
  • In the desulfonylation of N-indoles and N-azaindoles.
  • As a base in the synthesis of sodium acrylates from olefins and CO2.

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Flam. Sol. 1 - Self-heat. 1 - Skin Corr. 1B

supp_hazards

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 1

flash_point_f

57.2 °F

flash_point_c

14 °C

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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β-Hydrogen-Containing Sodium Alkoxides as Suitable Bases in Palladium-Catalyzed Aminations of Aryl Halides
Prashad M, et al.
The Journal of Organic Chemistry, 65(8), 2612-2614 (2000)
Desulfonylation of Indoles and 7-Azaindoles Using Sodium tert-Butoxide
Chaulet C, et al.
Synlett, 2010(10), 1481-1484 (2010)
tert-Butoxide-Mediated C-H Bond Arylation of Aromatic Compounds with Haloarenes
Yanagisawa S and Itami K
ChemCatChem, 3(5), 827-829 (2011)
Synthesis of acrylates from olefins and CO2 using sodium alkoxides as bases
Manzini S, et al.
Catalysis Today, 281(10), 379-386 (2017)
Palladium-catalyzed formation of aryl tert-butyl ethers from unactivated aryl halides
Parrish CA and Buchwald SL
The Journal of Organic Chemistry, 66(7), 2498-2500 (2001)

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