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359270

Sodium tert-butoxide

Name: Sodium <I>tert</I>-butoxide
Brand: ALDRICH

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

Assay:

97%

Form:

powder, crystals or chunks

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Properties

vapor pressure

0.0000026 hPa ( 50 °C)

assay

97%

form

powder, crystals or chunks

density

1,025 g/cm³ at 20 °C

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

Description

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.

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pictograms

GHS02,GHS05

signalword

Danger

hcodes

H228,H251,H314

pcodes

P210 - P235 - P260 - P280 - P303 + P361 + P353 - P305 + P351 + P338

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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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)

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)

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Global Trade Item Number

SKU	GTIN
359270-100G	04061831813166
359270-500G	04061831813180
359270-25G	04061831813173
359270-5G	04061831813197
359270-1.5KG	04061831813159