(S)-(-)-1,1'-Bi-2-naphthol
Synonym(s):(−)-2,2′-Dihydroxy-1,1′-dinaphthyl;(S)-(−)-1,1′-Binaphthalene-2,2′-diol;(S)-BINOL;(R)-(+)-1,1′-Binaphthyl-2,2′-diol;(R)-(+)-2,2′-Dihydroxy-1,1′-binaphthyl
- CAS NO.:18531-99-2
- Empirical Formula: C20H14O2
- Molecular Weight: 286.32
- MDL number: MFCD00004068
- EINECS: 606-050-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-12-24 21:24:35
What is (S)-(-)-1,1'-Bi-2-naphthol?
Chemical properties
white to light yellow crystal powde
The Uses of (S)-(-)-1,1'-Bi-2-naphthol
Chiral ligand.
The Uses of (S)-(-)-1,1'-Bi-2-naphthol
(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
What are the applications of Application
(S)-(?)-1,1′-Bi-2-naphthol is a chiral auxiliary for asymmetric ketone reduction
Definition
ChEBI: (S)-(-)-1,1'-Bi-2-naphthol is a member of naphthols.
Purification Methods
Dissolve it in cold 2.5N NaOH, extract with CH2Cl2, and acidify with 5% HCl. Collect the white precipitate and recrystallise it from aqueous EtOH and dry it in a vacuum [Akimoto & Yamada Tetrahedron 27 5999 1971]. It is optically stable in dioxane-water (100o/24hours). Racemisation: 72% in 1.2N HCl at 100o/24hours and 68% in 0.67M KOH in BuOH at 118o/23hours [Kyba et al. J Am Chem Soc 95 2693 1973]. It has also been crystallised from *C6H6 (solubility is 1%) using Norite or aqueous EtOH after chromatography through silica gel, eluting with Me2CO/*C6H6. [Kyba et al. J Org Chem 42 4173 1977; see also Brussee & Jansen Tetrahedron Lett 24 3261 1983, Akimoto & Yamada Tetrahedron 27 5999 1971, Beilstein 6 IV 7020.]
Properties of (S)-(-)-1,1'-Bi-2-naphthol
Melting point: | 215-218 °C |
Boiling point: | 388.69°C (rough estimate) |
alpha | -35.5 º (c=1, THF) |
Density | 1 g/cm3 |
refractive index | -36.0 ° (C=1, THF) |
storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
solubility | dioxane: 50 mg/mL, clear |
form | Crystals or Crystalline Powder |
pka | 8.29±0.50(Predicted) |
color | White to light gray |
optical activity | [α]22/D 34°, c = 1 in THF |
Merck | 14,1226 |
BRN | 3592999 |
CAS DataBase Reference | 18531-99-2(CAS DataBase Reference) |
Safety information for (S)-(-)-1,1'-Bi-2-naphthol
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for (S)-(-)-1,1'-Bi-2-naphthol
Abamectin manufacturer
Evans Fine Chem
JSK Chemicals
SOLFYN INTERNATIONAL LLP
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