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Merck
CN

726435

(1R)-2,2′-Bis[(S)-(4-methylphenyl)sulfinyl]-1,1′-binaphthalene

97%

Synonym(s):

(M,S,S)-1,1′-Binaphthalene-2,2′-diyl-bis(p-tolylsulfoxide), (M,S,S)-pTol-BINASO, (R)-2,2′-Bis-((S)-toluene-4-sulfinyl)-[1,1′]binaphthalenyl

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About This Item

Empirical Formula (Hill Notation):
C34H26O2S2
CAS Number:
722455-72-3
Molecular Weight:
530.70
NACRES:
NA.22
PubChem Substance ID:
329764236
UNSPSC Code:
12352005
MDL number:
MFCD18427912

Key Documents

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InChI

1S/C34H26O2S2/c1-23-11-17-27(18-12-23)37(35)31-21-15-25-7-3-5-9-29(25)33(31)34-30-10-6-4-8-26(30)16-22-32(34)38(36)28-19-13-24(2)14-20-28/h3-22H,1-2H3/t37-,38-/m0/s1

SMILES string

Cc1ccc(cc1)S(=O)c2ccc3ccccc3c2-c4c(ccc5ccccc45)S(=O)c6ccc(C)cc6

InChI key

GAWRHNNPYUEUOO-UWXQCODUSA-N

assay

≥96.5% (HPLC), 97%

form

powder

optical purity

ee: ≥97.0%

Application

(1R)-2,2′-Bis[(S)-(4-methylphenyl)sulfinyl]-1,1′-binaphthalene (p-tolyl-BINASO) is a bis-sulfoxide ligand that can be used to prepare cationic palladium and platinum complexes. These complexes are employed as catalysts in hydroboration and diboration reactions. It can also be used to prepare the precatalyst [p-tol-BINASO}RhCl]2 for the synthesis of chiral arylcycloketones by the 1,4-addition reaction of arylboronic acids to cyclic α,β-unsaturated ketones.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBH7941V
BCBB6289V
BCBB6289

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Synthesis, structure, and catalytic studies of palladium and platinum bis-sulfoxide complexes
Drinkel EE, et al.
Organometallics, 33(3), 627-636 (2014)
Disulfoxide ligands in rhodium catalyzed asymmetric 1,4-addition: first studies and future directions.
Mariz, R., et al.
Chimia, 63, 508-511 (2009)
A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins
Mariz R, et al.
Journal of the American Chemical Society, 130(7), 2172-2173 (2008)
A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins.
Ronaldo Mariz et al.
Journal of the American Chemical Society, 130(7), 2172-2173 (2008-01-29)

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