Introduction：Basic information about (S)-(-)-1,1'-Bi-2-naphthol CAS 18531-99-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
(S)-(-)-1,1'-Bi-2-naphthol Basic information
| Product Name: | (S)-(-)-1,1'-Bi-2-naphthol |
| Synonyms: | (R)-(+)-2,2'-DIHYDROXY-1,1'-BINAPHTHYL;(s)-(-)-1,1’-bi-2-nanphthol;1,1'-BI-2,2'-NAPHTHOLS;[1,1']BINAPHTHALENYL-2,2'-DIOL;(+/-)-1,1'-BINAPHTHALENE-2,2'-DIOL;(S)-(-)-BINOL(S)-(-)-2,2'-Dihydroxy-1,1'-binaphthyl;(S)-(-)-1,1''-BINAPHTHYL-2,2''-DIOL FOR SY;(S)-1,1'-Binaphthalene-2,2'-diol, (S)-BINOL |
| 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 |
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(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 |
| pka | 8.29±0.50(Predicted) |
| form | Crystals or Crystalline Powder |
| color | White to light gray |
| Optical Rotation | [α]22/D 34°, c = 1 in THF |
| Merck | 14,1226 |
| BRN | 3592999 |
| InChI | 1S/C20H14O2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H |
| InChIKey | PPTXVXKCQZKFBN-UHFFFAOYSA-N |
| SMILES | Oc1ccc2ccccc2c1-c3c(O)ccc4ccccc34 |
| CAS DataBase Reference | 18531-99-2(CAS DataBase Reference) |
Safety Information
| 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 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2 |
(S)-(-)-1,1'-Bi-2-naphthol Usage And Synthesis
| Chemical Properties | white to light yellow crystal powde |
| Uses | Chiral ligand. |
| 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. |
| 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
| Raw materials | Ethanol-->Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->Toluene-->Phosphorus oxitrichloride-->Triethylamine-->Benzene-->2-Naphthol-->Iron chloride hexahydrate-->L-1-Phenylethylamine-->Copper(II) chloride dihydrate-->(R)-(+)-1-Phenylethylamine |
| Preparation Products | (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL-->(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl-->(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL |
