Skip to Content
Merck
All Photos(6)

Key Documents

View All Documentation

359270

Sigma-Aldrich

Sodium tert-butoxide

97%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(6)

About This Item

Linear Formula:
NaOC(CH3)3
CAS Number:
865-48-5
Molecular Weight:
96.10
Beilstein:
3654215
EC Number:
212-741-9
MDL number:
MFCD00040575
UNSPSC Code:
12352107
PubChem Substance ID:
24862063
NACRES:
NA.22

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

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
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H228,H251,H314

Hazard Classifications

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

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

Flash Point(F)

57.2 °F

Flash Point(C)

14 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service