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(S)-(−)-1,1′-Bi(2-naphthol)

ALDRICH/246956 - 99%

Synonym: (−)-2,2′-Dihydroxy-1,1′-dinaphthyl; (S)-(−)-1,1′-Binaphthalene-2,2′-diol; (S)-BINOL

CAS Number: 18531-99-2
Empirical Formula (Hill Notation): C20H14O2
Molecular Weight: 286.32
MDL Number: MFCD00004068
Linear Formula: HOC10H6C10H6OH
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-246956-1G 1 g
 $51.50
1/EA		 Add To Favorites
45-246956-5G 5 g
 $64.50
1/EA		 Add To Favorites
45-246956-25G 25 g
 $77.50
1/EA		 Add To Favorites
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 246956-1G
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 246956-5G

 

assay 99%
InChI 1S/C20H14O2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H
InChI key PPTXVXKCQZKFBN-UHFFFAOYSA-N
mp 208-210 °C (lit.)
optical activity [α]22/D −34°, c = 1 in THF
optical purity ee: 99% (HPLC)
Quality Level 100 
SMILES string Oc1ccc2ccccc2c1-c3c(O)ccc4ccccc34
Application: (S)-BINOL ligand in combination with titanium(IV) isopropoxide, forms (S)-(-)-BINOL-Ti complex, which is an effective chiral catalyst for:
• asymmetric addition of alkynylzinc to unactivated ketones
• enantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilines
• asymmetric aryl transfers from triaryl(tetrahydrofuran)aluminum reagents to a wide variety of ketones
It can also react with zirconium(IV) isopropoxide isopropanol complex to form a chiral Lewis acid catalyst for the facile enantioselective allylation of aldehydes by allyltributyltin.
Application: Precursor to phosphoramidite catalyst employed in a conversion of allylic alcohols to allylic amines.
Packaging: 1, 5, 25 g in glass bottle
Purity 99%
mp 208-210 °C (lit.)
UNSPSC 12352005

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