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| | (S)-(-)-1,1'-Bi-2-naphthol Basic information |
| Product Name: | (S)-(-)-1,1'-Bi-2-naphthol | | Synonyms: | AKOS 90560;S-(-)-1,1'-Bi-2-naphthol,99%(S)-BINOL;1,1-Binaphthalene-2,2-diol, (1S)-;S-BINOL/S-(-)-1.1''-BINAPHTHYL-2.2''-DIOL;(S)-(-)-1,1'-Bi-2-naphtol;S-(-)-2,2''-DIHYDROXY-1,1''-DINAPHTHYL (S)-BINOL;(S)-1,1 -BI-2-NAPHTHOL ***REVERSE***;S-1,1-Bi-2-Naphtho | | CAS: | 18531-99-2 | | MF: | C20H14O2 | | MW: | 286.32 | | EINECS: | 606-050-5 | | Product Categories: | chiral;Alcohols and Derivatives;Chiral Reagent;CHIRAL COMPOUNDS;Chiral Compound;Peptide;Asymmetric Synthesis;Synthetic Organic Chemistry;blocks;BuildingBlocks;Intermediates of Dyes and Pigments;BINOL Series;Chiral Oxygen | | Mol File: | 18531-99-2.mol |  |
| | (S)-(-)-1,1'-Bi-2-naphthol Chemical Properties |
| Melting point | 215-218 °C | | alpha | -35.5 º (c=1, THF) | | Boiling point | 388.69°C (rough estimate) | | 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) |
| Hazard Codes | T,Xi | | Risk Statements | 25-36-36/37/38 | | Safety Statements | 26-45-24/25-36 | | RIDADR | UN 2811 6.1/PG 3 | | WGK Germany | 3 | | RTECS | DU3106100 | | F | 10 | | TSCA | No | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29072990 |
| | (S)-(-)-1,1'-Bi-2-naphthol Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powde | | Uses | (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. | | Uses | Chiral ligand. | | 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.] |
| | (S)-(-)-1,1'-Bi-2-naphthol Preparation Products And Raw materials |
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