423939
Phenyl trifluoromethanesulfonate
98%
Synonym(s):
Phenyl triflate
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About This Item
Linear Formula:
C6H5SO3CF3
CAS Number:
Molecular Weight:
226.17
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
98%
Form:
liquid
Quality Level
assay
98%
form
liquid
refractive index
n20/D 1.435 (lit.)
bp
99-100 °C/60 mmHg (lit.)
density
1.396 g/mL at 25 °C (lit.)
functional group
fluoro, triflate
SMILES string
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
InChI key
GRJHONXDTNBDTC-UHFFFAOYSA-N
General description
Phenyl trifluoromethanesulfonate (phenyl triflate) is an aryl fluorosulphonate. It has been synthesized by the reaction of phenol with fluorosulphonic anhydride.
Application
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Skin Corr. 1B
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
flash_point_f
159.8 °F - closed cup
flash_point_c
71 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 423939-5ML | 04061837247682 |
| 423939-25ML | 04061837247675 |