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425575

Sigma-Aldrich

2-Naphthyl trifluoromethanesulfonate

97%

Synonym(s):

2-Naphthyl triflate

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About This Item

Linear Formula:
CF3SO3C10H7
CAS Number:
3857-83-8
Molecular Weight:
276.23
MDL number:
MFCD00192341
UNSPSC Code:
12352100
PubChem Substance ID:
24866643
NACRES:
NA.22

assay

97%

form

solid

mp

30-32 °C (lit.)

functional group

fluoro
triflate

SMILES string

FC(F)(F)S(=O)(=O)Oc1ccc2ccccc2c1

InChI

1S/C11H7F3O3S/c12-11(13,14)18(15,16)17-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H

InChI key

MDWRQYBWVTXIIJ-UHFFFAOYSA-N

General description

2-Naphthyl trifluoromethanesulfonate (2-naphthyl triflate) is an aryl triflate. Its ruthenium-catalyzed conversion to 2-bromonaphthalene has been reported.[1]

Application

2-Naphthyl trifluoromethanesulfonate (2-naphthyl triflate) may be used as an arylating agent in the arylation of 1-(methoxycarbonyl)-2,5-dihydropyrrole by Heck reaction.[2] It may be used as a substrate for coupling with Reformatsky reagent BrZnCH(CH3)(COOtC4H9) in the presence of “reduced” dichlorobis(1,1-diphenylphosphino)ferrocene catalyst.[3]

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKBS4032V
06001LU
20115MS
00426JG

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Influence of the catalyst on the Pd0-mediated reactions of BrZnCH(CH3) COOtBu with vinyl and aryl triflates.
Orsini F, et al.
Journal of Organometallic Chemistry, 367(3), 375-382 (1989)
Regiochemical control and suppression of double bond isomerization in the Heck arylation of 1-(methoxycarbonyl)-2, 5-dihydropyrrole.
Sonesson C, et al.
The Journal of Organic Chemistry, 61(14), 4756-4763 (1996)
Xiaoqiang Shen et al.
Journal of the American Chemical Society, 132(40), 14076-14078 (2010-09-23)
The palladium-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) has been developed using dialkylbiaryl phosphine ligands. A variety of aryl, heteroaryl, and vinyl halides can be prepared via this method in good to

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