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359270

Sigma-Aldrich

Sodium tert-butoxide

97%

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:
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

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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

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’.

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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)

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