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280704

Sigma-Aldrich

Sodium tert-pentoxide

95%

Synonym(s):

NaOt-Am, tert-Amyl alcohol sodium salt, Sodium tert-amoxide

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About This Item

Linear Formula:
NaOC(CH3)2CH2CH3
CAS Number:
14593-46-5
Molecular Weight:
110.13
Beilstein:
3983987
EC Number:
238-639-4
MDL number:
MFCD00064245
UNSPSC Code:
12352001
PubChem Substance ID:
24856952
NACRES:
NA.22

Assay

95%

SMILES string

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

InChI

1S/C5H11O.Na/c1-4-5(2,3)6;/h4H2,1-3H3;/q-1;+1

InChI key

CGRKYEALWSRNJS-UHFFFAOYSA-N

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Application

Sodium tert-pentoxide (NaOt-Am) is a commonly used base in the deoxycyanamidation of alcohols and in the N-cyanation of secondary amines. It can also be used in the preparation of complex reducing agents to reduce 1-halonaphthalenes and substituted halobenzenes to corresponding naphthalenes and benzenes.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Dam. 1 - Flam. Sol. 1 - Self-heat. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

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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Deoxycyanamidation of Alcohols with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS).
Ayres J N, et al.
Organic Letters, 19(14), 3835-3838 (2017)
N-Cyanation of Secondary Amines Using Trichloroacetonitrile.
Ayres J N, et al.
Organic Letters, 18(21), 5528-5531 (2016)
Activation of reducing agents: Sodium hydride-containing ?complex reducing agents?: I. Reduction of aromatic halides.
Guillaumet G, et al.
Journal of Organometallic Chemistry, 92(1), 43-47 (1975)
Brandon K Tate et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(28), 10160-10169 (2015-06-11)
Alkoxide-bridged disilver cations react with dihydrogen to form hydride-bridged cations, releasing free alcohol. Hydrogenolysis of neutral silver fluorides affords hydride-bridged disilver cations as their bifluoride salts. These reactions proceed most efficiently when the supporting ligands are expanded N-heterocyclic carbenes (NHCs)

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