(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

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.

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.