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Merck
CN

359270

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
UNSPSC Code:
12352107
NACRES:
NA.22
PubChem Substance ID:
24862063
EC Number:
212-741-9
Beilstein/REAXYS Number:
3654215
MDL number:
MFCD00040575

Key Documents

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Product Name

Sodium tert-butoxide, 97%

InChI key

MFRIHAYPQRLWNB-UHFFFAOYSA-N

InChI

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

SMILES string

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

vapor pressure

0.0000026 hPa ( 50 °C)

assay

97%

density

1,025 g/cm3 at 20 °C

Quality Level

200

form

powder, crystals or chunks

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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

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

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ7326
MKCZ5279
STBK5592
STBK1614
STBJ9505

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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)
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)
Activation and discovery of earth-abundant metal catalysts using sodium tert-butoxide.
Docherty JH, et al.
Nature Chemistry, 9(6), 595-595 (2017)
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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