(R)-(+)-3,3′-Bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-bi-2-naphthol

Name: (<I>R</I>)-(+)-3,3′-Bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-bi-2-naphthol
Brand: ALDRICH
Price: 79.5 USD
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95%

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About This Item

Empirical Formula (Hill Notation):

C₃₆H₁₈F₁₂O₂

CAS Number:

756491-54-0

Molecular Weight:

710.51

MDL number:

MFCD08689862

UNSPSC Code:

12352005

PubChem Substance ID:

24885224

NACRES:

NA.22

Key Documents

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Quality Level

100

assay

95%

form

solid

optical activity

[α]22/D 45°, c = 1 in chloroform

mp

216-220 °C

functional group

fluoro

SMILES string

FC(F)(F)c1cc(cc(c1)c2cc3c(c(c2O)c4c5c(cc(c4O)c6cc(cc(c6)C(F)(F)F)C(F)(F)F)cccc5)cccc3)C(F)(F)F

InChI

1S/C36H18F12O2/c37-33(38,39)21-9-19(10-22(15-21)34(40,41)42)27-13-17-5-1-3-7-25(17)29(31(27)49)30-26-8-4-2-6-18(26)14-28(32(30)50)20-11-23(35(43,44)45)16-24(12-20)36(46,47)48/h1-16,49-50H

Inchi Key

PGXMYJSTCAQJBY-UHFFFAOYSA-N

Related Categories

Catalysts

Chemistry & Biochemicals

Chiral Catalysts & Ligands

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This Item	681539	690007	674737
Sigma-Aldrich 674591 (R)-(+)-3,3′-Bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-bi-2-naphthol	Sigma-Aldrich 681539 (S)-(–)-3-3′-Bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-bi-2-naphthol	Sigma-Aldrich 690007 (S)-3,3′-Bis(2,4,6-triisopropylphenyl)-1,1′-bi-2-naphthol	Sigma-Aldrich 674737 (R)-3,3′-Bis(triphenylsilyl)-1,1′-bi-2-naphthol
assay 95%	assay 95%	assay 95% (HPLC)	assay 96%
functional group fluoro	functional group fluoro	functional group -	functional group -
form solid	form (Powder or Crystals or Solid or Chunks)	form solid	form solid
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
mp 216-220 °C	mp 215-219 °C	mp -	mp 103-145 °C
optical activity [α]22/D 45°, c = 1 in chloroform	optical activity [α]22/D -56°, c = 1 in chloroform	optical activity -	optical activity [α]20/D +114°, c = 1 in chloroform

Application

Precursor to a chiral Bronsted acid (680184) used to catalyze an enantioselective aza Diels-Alder reaction providing bicyclic lactams.[1] Rare earth metal complexes of this chiral binapthol catalyze an intramolecular hydroamination of amino olefins leading to chiral pyrrolidines.[2]

Pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Brønsted acids.

Hua Liu et al.

Organic letters, 8(26), 6023-6026 (2006-12-15)

[Structure: see text] The first chiral Brønsted acid-catalyzed asymmetric direct aza hetero-Diels-Alder reaction has been described. The phosphoric acids, prepared from binol and H8-binol derivatives, have shown catalytic ability for the reaction of cyclohexenone with N-PMP-benzaldimine. A chiral phosphoric acid

3,3'-Bis(trisarylsilyl)-substituted binaphtholate rare earth metal catalysts for asymmetric hydroamination.

Denis V Gribkov et al.

Journal of the American Chemical Society, 128(11), 3748-3759 (2006-03-16)

Chiral 3,3'-bis(trisarylsilyl)-substituted binaphtholate rare earth metal complexes (R)-[Ln{Binol-SiAr3}(o-C6H4CH2NMe2)(Me2NCH2Ph)] (Ln = Sc, Lu, Y; Binol-SiAr3 = 3,3'-bis(trisarylsilyl)-2,2'-dihydroxy-1,1'-binaphthyl; Ar = Ph (2-Ln), 3,5-xylyl (3-Ln)) and (R)-[La{Binol-Si(3,5-xylyl)3}{E(SiMe3)2}(THF)2] (E = CH (4a), N (4b)) are accessible via facile arene, alkane, and amine elimination. They

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BINOL and Derivatives

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