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690007

Sigma-Aldrich

(S)-3,3′-Bis(2,4,6-triisopropylphenyl)-1,1′-bi-2-naphthol

95% (HPLC)

Synonym(s):

(1S)-3,3′-Bis[2,4,6-tris(1-methylethyl)phenyl]-1,1′-binaphthalene-2,2′-diol

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About This Item

Empirical Formula (Hill Notation):
C50H58O2
CAS Number:
Molecular Weight:
690.99
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

assay

95% (HPLC)

form

solid

optical purity

ee: ≥99.0

SMILES string

CC(C)c1cc(C(C)C)c(c(c1)C(C)C)-c2cc3ccccc3c(c2O)-c4c(O)c(cc5ccccc45)-c6c(cc(cc6C(C)C)C(C)C)C(C)C

InChI

1S/C50H58O2/c1-27(2)35-23-39(29(5)6)45(40(24-35)30(7)8)43-21-33-17-13-15-19-37(33)47(49(43)51)48-38-20-16-14-18-34(38)22-44(50(48)52)46-41(31(9)10)25-36(28(3)4)26-42(46)32(11)12/h13-32,51-52H,1-12H3

InChI key

BCAHCEFAVPAFSH-UHFFFAOYSA-N

Application

(S)-3,3′-Bis(2,4,6-triisopropylphenyl)-1,1′-bi-2-naphthol can be used as a reactant to prepare BINOL-based chiral N-triflyl thiophosphoramides as chiral Bronsted acid catalysts for the asymmetric synthesis of α-substituted cycloalkanones via enantioselective hydrolysis of alicyclic silyl enol ethers.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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A Bronsted acid catalyst for the enantioselective protonation reaction
Cheon CH and Yamamoto H
Journal of the American Chemical Society, 130(29), 9246-9247 (2008)

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