(R)-(+)-1,1'-Bi-2-naphthol

Synonym(s):(+)-2,2′-Dihydroxy-1,1′-dinaphthyl;(R)-(+)-1,1′-Binaphthalene-2,2′-diol;(R)-BINOL

CAS NO.：18531-94-7
Empirical Formula: C20H14O2
Molecular Weight: 286.32
MDL number: MFCD00004068
EINECS: 606-048-4
SAFETY DATA SHEET (SDS)
Update Date: 2025-01-27 09:38:02

What is (R)-(+)-1,1'-Bi-2-naphthol?

Chemical properties

white to light yellow crystal powde

The Uses of (R)-(+)-1,1'-Bi-2-naphthol

Chiral binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins.

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 (R)-(+)-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	1.301
refractive index	36.0 ° (C=1, THF)
storage temp.	Store below +30°C.
solubility	dioxane: 50 mg/mL, clear
form	Powder
pka	8.29±0.50(Predicted)
color	white to off-white
optical activity	[α]21/D +34°, c = 1 in THF
Water Solubility	Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL.
Merck	14,1226
BRN	3616837
CAS DataBase Reference	18531-94-7(CAS DataBase Reference)

Safety information for (R)-(+)-1,1'-Bi-2-naphthol

Signal word	Danger
Pictogram(s)	Skull and Crossbones Acute Toxicity GHS06
GHS Hazard Statements	H301:Acute toxicity,oral 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.