423939
Phenyl trifluoromethanesulfonate
98%
Synonym(s):
Phenyl triflate
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About This Item
Linear Formula:
C6H5SO3CF3
CAS Number:
Molecular Weight:
226.17
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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.)
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
Related Categories
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Oral - Skin Corr. 1B
Storage Class Code
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
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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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