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790885

Sigma-Aldrich

(R)-3,3′-Dibromo-1,1′-binaphthyl-2,2′-disulfonimide toluene complex

97%

Synonym(s):

(11bR)-2,6-Dibromodinaphtho[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):
(C20H11Br2NO4S2)2 · C6H5CH3
Molecular Weight:
1198.63
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

solid

reaction suitability

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

mp

306-310 °C

functional group

bromo
phenyl

SMILES string

CC1=CC=CC=C1.BrC2=CC(C=CC=C3)=C3C(C4=C(C=CC=C5)C5=CC(Br)=C4S6(=O)=O)=C2S(N6)(=O)=O.BrC7=CC(C=CC=C8)=C8C(C9=C(C=CC=C%10)C%10=CC(Br)=C9S%11(=O)=O)=C7S(N%11)(=O)=O

InChI

1S/2C20H11Br2NO4S2.C7H8/c2*21-15-9-11-5-1-3-7-13(11)17-18-14-8-4-2-6-12(14)10-16(22)20(18)29(26,27)23-28(24,25)19(15)17;1-7-5-3-2-4-6-7/h2*1-10,23H;2-6H,1H3

InChI key

WQYRPPIFPJBANM-UHFFFAOYSA-N

Application

Chiral Bronsted acid amenable to modification at the 3 and 3′ positions.

A Powerful Chiral Counteranion Motif for Asymmetric Catalysis

Chiral Sulfonimide as a Brønsted Acid Organocatalyst for Asymmetric Friedel-Crafts Alkylation of Indoles with Imines

A href="http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201300956/abstract" target="_blank">Chiral N-Fluorodibenzenesulfonimide Analogues for Enantioselective Electrophilic Fluorination and Oxidative Fluorination

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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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