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423939

Sigma-Aldrich

Phenyl trifluoromethanesulfonate

98%

Sinonimo/i:

Phenyl triflate

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About This Item

Formula condensata:
C6H5SO3CF3
Numero CAS:
17763-67-6
Peso molecolare:
226.17
Numero MDL:
MFCD00192399
Codice UNSPSC:
12352100
ID PubChem:
24866540
NACRES:
NA.22

Saggio

98%

Forma fisica

liquid

Indice di rifrazione

n20/D 1.435 (lit.)

P. eboll.

99-100 °C/60 mmHg (lit.)

Densità

1.396 g/mL at 25 °C (lit.)

Gruppo funzionale

fluoro
triflate

Stringa SMILE

FC(F)(F)S(=O)(=O)Oc1ccccc1

InChI

1S/C7H5F3O3S/c8-7(9,10)14(11,12)13-6-4-2-1-3-5-6/h1-5H
GRJHONXDTNBDTC-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

Phenyl trifluoromethanesulfonate (phenyl triflate) is an aryl fluorosulphonate. It has been synthesized by the reaction of phenol with fluorosulphonic anhydride.

Applicazioni

Phenyl trifluoromethanesulfonate (phenyl triflate) may be used in the following studies:
  • As an arylating agent for the asymmetric α-arylation of ketones catalyzed by Pd(dba)2 and difluorphos.
  • As a reactant in the one pot synthesis of carbazoles by palladium-catalyzed N-arylation of anilines with phenyl triflate followed by oxidative coupling.
  • Synthesis of N-(2,6-diarylbenzoyl)anilines by diarylation of benzanilides with phenyl triflate in the presence of palladium-based catalyst.
  • As an arylating agent in the synthesis of (R)-2-phenyl-2,3-dihydrofuran by the arylation of 2,3-dihydrofuran.

Pittogrammi

Skull and crossbonesCorrosion
GHS06,GHS05

Avvertenze

Danger

Indicazioni di pericolo

H301 + H311,H314

Classi di pericolo

Acute Tox. 3 Oral - Skin Corr. 1B

Codice della classe di stoccaggio

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

159.8 °F - closed cup

Punto d’infiammabilità (°C)

71 °C - closed cup

Dispositivi di protezione individuale

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificati d'analisi (COA)

Lot/Batch Number
MKBN7716V
MKBF4386
45297MJ
10617LH
03013DE

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One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling.
Watanabe T, et al.
Chemical Communications (Cambridge, England), 43, 4516-4518 (2007)
Palladium-catalyzed asymmetric arylation of 2, 3-dihydrofuran with phenyl triflate. A novel asymmetric catalysis involving a kinetic resolution process.
Ozawa F, et al.
Organometallics, 12(10), 4188-4196 (1993)
Palladium cross-coupling reactions of aryl fluorosulfonates: an alternative to triflate chemistry.
Roth GP and Fuller CE.
The Journal of Organic Chemistry, 56(11), 3493-3496 (1991)
Xuebin Liao et al.
Journal of the American Chemical Society, 130(1), 195-200 (2007-12-14)
The asymmetric alpha-arylation of ketones with aryl triflates is described, and the use of this electrophile with nickel and palladium catalysts containing a segphos derivative increases substantially the scope of highly enantioselective arylations of ketone enolates. The combination of aryl
Regioselective arylation of benzanilides with aryl triflates or bromides under palladium catalysis.
Kametani Y, et al.
Tetrahedron Letters, 41(15), 2655-2658 (2000)

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