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423939

Sigma-Aldrich

Phenyl trifluoromethanesulfonate

98%

Sinônimo(s):

Phenyl triflate

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About This Item

Fórmula linear:
C6H5SO3CF3
Número CAS:
17763-67-6
Peso molecular:
226.17
Número MDL:
MFCD00192399
Código UNSPSC:
12352100
ID de substância PubChem:
24866540
NACRES:
NA.22

Ensaio

98%

forma

liquid

índice de refração

n20/D 1.435 (lit.)

pb

99-100 °C/60 mmHg (lit.)

densidade

1.396 g/mL at 25 °C (lit.)

cadeia de caracteres SMILES

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

chave InChI

GRJHONXDTNBDTC-UHFFFAOYSA-N

Categorias relacionadas

Descrição geral

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

Aplicação

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.

Pictogramas

CorrosionSkull and crossbones
GHS05,GHS06

Palavra indicadora

Danger

Frases de perigo

H301 + H311 - H314

Classificações de perigo

Acute Tox. 3 Oral - Skin Corr. 1B

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

159.8 °F - closed cup

Ponto de fulgor (°C)

71 °C - closed cup

Equipamento de proteção individual

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

Certificados de análise (COA)

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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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