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726443

Sigma-Aldrich

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

≥96.5% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C34H26O2S2
CAS Number:
722455-73-4
Molecular Weight:
530.70
MDL number:
MFCD18427912
UNSPSC Code:
12352005
PubChem Substance ID:
329764238
NACRES:
NA.22

Assay

≥96.5% (HPLC)

form

powder

optical activity

[α]/D -750±25°, c = 1 in chloroform

SMILES string

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

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

InChI key

GAWRHNNPYUEUOO-UWXQCODUSA-N

Application

(1S)-2,2′-Bis[(S)-(4-methylphenyl)sulfinyl]-1,1′-binaphthalene can be used as a ligand to prepare:
  • Pd and Pt metal complexes, which are used as catalysts in hydroboration and diboration reactions.
  • Rh metal complex catalysts for asymmetric addition reaction of aryl boronic acids with olefins.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Analysis Note

diastereometric purity ≥97.0%

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD8463V
BCBD8463
BCBB6287

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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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