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221163

Sigma-Aldrich

Silver(I) oxide

ReagentPlus®, 99%

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About This Item

Empirical Formula (Hill Notation):
Ag2O
CAS Number:
20667-12-3
Molecular Weight:
231.74
EC Number:
243-957-1
MDL number:
MFCD00003404
UNSPSC Code:
12352303
PubChem Substance ID:
329752249
NACRES:
NA.21

product line

ReagentPlus®

Assay

99%

form

powder or chunks

reaction suitability

reagent type: catalyst
core: silver

SMILES string

[Ag]O[Ag]

InChI

1S/2Ag.O

InChI key

KHJDQHIZCZTCAE-UHFFFAOYSA-N

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Application

Mediates monoprotection of symmetrical diols with alkyl halides in good to excellent yield.
Silver(I) oxide may be used to mediate the following processes:
  • Selective monoalkylation of symmetric diols in the presence of alkyl halide.
  • Palladium catalyzed cross-coupling of aryl- and alkenylsilanols with organic halides.
  • Palladium-catalyzed reaction of aryl and alkenyl halides with terminal alkynes to form arylated or alkenylated alkynes, respectively.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Statements

H271,H318,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Ox. Sol. 1

Storage Class Code

5.1A - Strongly oxidizing hazardous materials

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Highly selective silver (I) oxide mediated monoprotection of symmetrical diols
Bouzide A and Sauve G.
Tetrahedron Letters, 38(34), 5945-5948 (1997)
A New Transformation of Silanols. Palladium-Catalyzed Cross-Coupling with Organic Halides in the Presence of Silver (I) Oxide
Hirabayashi K, et al.
Organic Letters, 1(2), 299-302 (1999)
Eagleson M.
Concise Encyclopedia Chemistry, 90-90 (1994)
Non-Sonogashira-type palladium-catalyzed coupling reactions of terminal alkynes assisted by silver (I) oxide or tetrabutylammonium fluoride.
Mori A, et al.
Organic Letters, 2(19), 2935-2937 (2000)
Abderrahim Bouzide et al.
Organic letters, 4(14), 2329-2332 (2002-07-06)
[reaction: see text] The reaction of symmetrical diols and oligo(ethylene glycol)s with a stoichiometric amount of p-toluenesulfonyl chloride in the presence of silver(I) oxide and a catalytic amount of potassium iodide led selectively to the monotosylate derivatives in high yields.
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