Introduction：Basic information about (R)-(+)-1,1'-Bi-2-naphthol CAS 18531-94-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
(R)-(+)-1,1'-Bi-2-naphthol Basic information
| Product Name: | (R)-(+)-1,1'-Bi-2-naphthol |
| Synonyms: | (R)-(+)-BI-2-NAPHTHOL;(R)-[1,1']-Binaphth-2-ol, (R)-BINOL;(+)-2,2μ-Dihydroxy-1,1μ-dinaphthyl, (R)-(+)-1,1μ-Binaphthalene-2,2μ-diol, (R)-BINOL;(R)-(+)-1,1'-Bi-2-naphthol 99%;[aR,(+)]-1,1'-Binaphthalene-2,2'-diol;[aR,(+)]-Dinaphthol;R-(+)-1_Bi-2-naphthol;(R)-(+)-1,1'-Bi-2-na |
| CAS: | 18531-94-7 |
| MF: | C20H14O2 |
| MW: | 286.32 |
| EINECS: | 606-048-4 |
| Product Categories: | BINOL Series;Chiral Oxygen;chiral;Intermediates of Dyes and Pigments;Alcohols and Derivatives;Chiral Reagent;CHIRAL COMPOUNDS;Chiral Compound;Peptide;Asymmetric Synthesis;Synthetic Organic Chemistry |
| Mol File: | 18531-94-7.mol |
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(R)-(+)-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 | 1.301 |
| refractive index | 36.0 ° (C=1, THF) |
| storage temp. | Store below +30°C. |
| solubility | dioxane: 50 mg/mL, clear |
| pka | 8.29±0.50(Predicted) |
| form | Powder |
| color | white to off-white |
| Optical Rotation | [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 |
| 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 | 18531-94-7(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 | 29071590 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2 |
| Toxicity | LD50 orally in Rabbit: 113 mg/kg |
(R)-(+)-1,1'-Bi-2-naphthol Usage And Synthesis
| Chemical Properties | white to light yellow crystal powde |
| Uses | 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. |
| Synthesis | Racemic 1,1'-bi-2-naphthol is resolved via formation of a molecular inclusion complex. The racemate is heated with (S)-proline in acetonitrile under reflux. Upon cooling, a white solid (the molecular inclusion complex) precipitates and is filtered. The white solid is treated with ethanol to give inclusion complex crystals. These crystals are stirred in a two-phase ethyl acetate-water system. After separation, the organic phase is processed to yield enantiopure (S)-product. The acetonitrile filtrate is processed to yield enantiopure (R)-product. The aqueous phase allows recovery of (S)-proline. |
| 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.] |
(R)-(+)-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-->1,1'-Bi-2-naphthol |
| Preparation Products | (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one-->(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL-->(R)-(+)-TolBINAP-->(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl-->(R)-(-)-6,6'-Dibromo-1,1'-bi-2-naphthol-->R-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol |
