(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: 2024-11-28 18:20:31
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. |
Computed Descriptors for (R)-(+)-1,1'-Bi-2-naphthol
(R)-(+)-1,1'-Bi-2-naphthol manufacturer
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product: (R)-(+)-1,1'-Bi-2-naphthol
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