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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
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Quality Level

100

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[1] and in the N-cyanation of secondary amines.[2] It can also be used in the preparation of complex reducing agents to reduce 1-halonaphthalenes and substituted halobenzenes to corresponding naphthalenes and benzenes.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7801
MKCW4320
MKCW0635
MKCT3264
MKCQ5360

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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)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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