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440590

Sigma-Aldrich

(R)-(−)-1,1′-Bi-2-naphthol bis(trifluoromethanesulfonate)

97%

Synonym(s):

(R)-1,1′-Bi(2-naphthol) bis(trifluoromethanesulfonate), (R)-1,1′-Binaphthalene-2,2′-diyl bis(trifluoromethanesulfonate)

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About This Item

Linear Formula:
(CF3SO3C10H6-)2
CAS Number:
126613-06-7
Molecular Weight:
550.45
Beilstein:
4282753
MDL number:
MFCD00274615
UNSPSC Code:
12352005
PubChem Substance ID:
24867612
NACRES:
NA.22
Pricing and availability is not currently available.

Assay

97%

optical activity

[α]23/D −146°, c = 1 in chloroform

mp

82-85 °C (lit.)

SMILES string

FC(F)(F)S(=O)(=O)Oc1ccc2ccccc2c1-c3c(OS(=O)(=O)C(F)(F)F)ccc4ccccc34

InChI

1S/C22H12F6O6S2/c23-21(24,25)35(29,30)33-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)34-36(31,32)22(26,27)28/h1-12H

InChI key

OYJLCOSEYYZULE-UHFFFAOYSA-N

Application

(R)-(−)-1,1′-Bi-2-naphthol bis(trifluoromethanesulfonate) can be used:
  • In the synthesis of heterobidentate ligands for asymmetric catalysis.[1][2]
  • To prepare 2-(diphenylphosphino)-2′-alkoxy-1,1′-binaphthyls by reacting with bis(aryl) phosphonic acids.[3]
  • As a starting material for the synthesis of binaphthyl based rhodium catalysts used in the hydrogenation of styrene.[4]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
07906BQ
00411TI
16413ER

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Palladium-catalysed asymmetric allylic alkylation in the presence of a chiral `light fluorous? phosphine ligand
Cavazzini M, et al.
Chemical Communications (Cambridge, England), 13, 1220-1221 (2001)
Synthesis of chiral 2, 2′-bis (diphenylphosphino)-1, 1′-binaphthyl (BINAP) via a novel nickel-catalyzed phosphine insertion
Cai D, et al.
The Journal of Organic Chemistry, 59(23), 7180-7181 (1994)
New perfluorinated rhodium-BINAP catalysts and hydrogenation of styrene in supercritical CO2
Altinel H, et al.
Journal of Supercritical Fluids, 51(2), 202-208 (2009)
Novel heterobidentate ligands for asymmetric catalysis: Synthesis and rhodium-catalysed reactions of S-alkyl (R)-2-diphenylphosphino-1, 1′-binaphthyl-2′-thiol
Gladiali S, et al.
Tetrahedron Asymmetry, 5(7), 1143-1146 (1994)

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