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790850

Sigma-Aldrich

(S)-3,3′-Bis(4-trifluoromethylphenyl)-1,1′-binaphthyl-2,2′-disulfonimide

Synonym(s):

(11bS)-2,6-Bis[4-(trifluoromethyl)phenyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dithiazepine 3,3,5,5-tetraoxide

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About This Item

Empirical Formula (Hill Notation):
C34H19F6NO4S2
Molecular Weight:
683.64
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

form

solid

reaction suitability

reaction type: Aldol Reaction
reaction type: Allylation
reaction type: Carbonyl/Imine Addition
reaction type: Friedel-Crafts Alkylation

mp

340-360 °C

SMILES string

O=S(C1=C(C2=C(C=CC=C3)C3=CC(C4=CC=C(C(F)(F)F)C=C4)=C2S5(=O)=O)C6=C(C=CC=C6)C=C1C7=CC=C(C(F)(F)F)C=C7)(N5)=O

InChI

1S/C34H19F6NO4S2/c35-33(36,37)23-13-9-19(10-14-23)27-17-21-5-1-3-7-25(21)29-30-26-8-4-2-6-22(26)18-28(20-11-15-24(16-12-20)34(38,39)40)32(30)47(44,45)41-46(42,43)31(27)29/h1-18,41H

InChI key

FQLCMGCITBTGMR-UHFFFAOYSA-N

Application

Chiral Bronsted acid used in allylation of imines.

A Powerful Chiral Counteranion Motif for Asymmetric Catalysis

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Articles

Asymmetric counteranion-directed catalysis (ACDC) has a number of valuable applications in enantioselective synthesis.

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