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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.)

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.

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. 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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

425575-10G:
425575-VAR:
425575-BULK:
425575-2G:

Certificates of Analysis (COA)

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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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