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Key Documents

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176435

Sigma-Aldrich

Silver trifluoromethanesulfonate

≥99%

Sinonimo/i:

Silver triflate, Trifluoromethanesulfonic acid silver salt

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About This Item

Formula condensata:
CF3SO3Ag
Numero CAS:
2923-28-6
Peso molecolare:
256.94
Beilstein:
3598402
Numero CE:
220-882-2
Numero MDL:
MFCD00013226
Codice UNSPSC:
12161600
ID PubChem:
24850578
NACRES:
NA.22

Livello qualitativo

100

Saggio

≥99%

Forma fisica

powder

Impiego in reazioni chimiche

core: silver
reagent type: catalyst

Punto di fusione

286 °C (lit.)

Stringa SMILE

[Ag+].[O-]S(=O)(=O)C(F)(F)F

InChI

1S/CHF3O3S.Ag/c2-1(3,4)8(5,6)7;/h(H,5,6,7);/q;+1/p-1
QRUBYZBWAOOHSV-UHFFFAOYSA-M

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Categorie correlate

Applicazioni

Gold Catalysts — 21st Century ′Gold Rush′
Silver trifluoromethanesulfonate is a reactive triflating agent and source of soluble silver ions useful for formation of electrophilic onium species, and promotion of Friedel-Crafts, nucleophile alkene cyclization, and esterification reactions.
It can also be used:
  • To obtain olefins from secondary phosphates and thiophosphates.
  • As a reagent in the etherification of alcohols with primary alkyl halides under mild conditions.
  • To generate cationic rhodium catalysts from chlororhodium complexes for the hydrophosphination of acetylenes.
  • As a catalyst for the preparation of silyl ethers by hydrosilylation of aldehydes.

Pittogrammi

Corrosion
GHS05

Avvertenze

Danger

Indicazioni di pericolo

H315,H318

Classi di pericolo

Eye Dam. 1 - Skin Irrit. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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New synthetic methods for olefins from secondary phosphates and thiophosphates
Shimagaki M, et al.
Tetrahedron Letters, 36, 719-719 (1995)
Tetrahedron Letters, 35, 8111-8111 (1994)
Minoru Hayashi et al.
The Journal of organic chemistry, 71(24), 9248-9251 (2006-11-18)
A novel rhodium-catalyzed hydrophosphination of alkynes using a silylphosphine as a phosphino group source is described. A variety of alkynes, both terminal and internal ones with aryl, alkyl, and carboxyl groups, gave the corresponding alkenylphosphines in a highly regioselective and
Chemical Communications (Cambridge, England), 1359-1359 (2006)
Simbarashe Ngwerume et al.
The Journal of organic chemistry, 78(3), 920-934 (2012-12-29)
A novel gold-catalyzed method for the regioselective synthesis of highly substituted pyrroles directly from oximes and alkynes was developed via independent optimization of two key steps of the process. Importantly, a cationic gold(I) species was shown to activate multiple steps
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