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| | (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;Intermediates of Dyes and Pigments;Alcohols and Derivatives;chiral;Chiral Reagent;CHIRAL COMPOUNDS;Asymmetric Synthesis;Synthetic Organic Chemistry;Chiral Compound;Peptide | | Mol File: | 18531-94-7.mol |  |
| | (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 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) |
| 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 | | 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. | | 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 oxychloride-->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 |
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