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359270

Sigma-Aldrich

Sodium tert-butoxide

97%

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Synonym(s):
Sodium 2-methylpropan-2-olate, Sodium t-butoxide, Sodium tert-butanolate, Sodium tert-butylate
Linear Formula:
NaOC(CH3)3
CAS Number:
Molecular Weight:
96.10
Beilstein/REAXYS Number:
3654215
EC Number:
MDL number:
PubChem Substance ID:

assay

97%

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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1 of 4

This Item
7037888.18374702706
vibrant-m

359270

Sodium tert-butoxide

vibrant-m

703788

Sodium tert-butoxide

vibrant-m

8.18374

Sodium tert-butylate

vibrant-m

702706

Sodium tert-butoxide solution

assay

97%

assay

99.9%

assay

≥96.0% (acidimetric)

assay

-

Application

Sodium tert-butoxide may be used as a safe and effective alternative to sodium hydride for the coupling of hydroxyethyl adenine with diethyl p-toluenesulfonyloxymethanephosphonate to form 9-[2-(diethylphosphonomethoxy)ethyl]adenine (diethyl-PMEA), which is a key intermediate to prepare adefovir dipivoxil.
It can also be used:
  • To facilitate the coupling of aryl halides with benzene derivatives in the presence of 10-phenanthroline derivative.
  • To activate first-row transition-metal pre-catalysts.
  • As a base for the amination of aryl chlorides in the presence of a novel palladacyclic precatalyst.

pictograms

FlameCorrosion

signalword

Danger

Hazard Classifications

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

supp_hazards

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

ppe

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


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Customers Also Viewed

Activation and discovery of earth-abundant metal catalysts using sodium tert-butoxide.
Docherty JH, et al.
Nature Chemistry, 9(6), 595-595 (2017)
tert-Butoxide-mediated arylation of benzene with aryl halides in the presence of a catalytic 1, 10-phenanthroline derivative.
Shirakawa E, et al.
Journal of the American Chemical Society, 132(44), 15537-15539 (2010)
Process optimization in the synthesis of 9-[2-(diethylphosphonomethoxy) ethyl] adenine: replacement of sodium hydride with sodium tert-butoxide as the base for oxygen alkylation.
Yu RH, et al.
Organic Process Research & Development, 3(1), 53-55 (1999)
An air and thermally stable one-component catalyst for the amination of aryl chlorides.
Zim D and Buchwald SL.
Organic Letters, 5(14), 2413-2415 (2003)

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