(R)-(+)-1,1'-BI-2-NAPHTHOL
(R)-(+)-1,1'-Bi-2-naphthol
CAS: 18531-94-7
Molecular Formula: C20H14O2
(R)-(+)-1,1'-BI-2-NAPHTHOL - Names and Identifiers
| Name | (R)-(+)-1,1'-Bi-2-naphthol |
| Synonyms | (R)-(+)-Binol [aR,(+)]-Dinaphthol (R)-(+)-1,1'-Bi-2-na R-(+)-1_Bi-2-naphthol (R)-(+)-BI-2-NAPHTHOL R-(+)-1,1'-Bi-2-Naphthol (R)-(+)-1,1-Bi-2-Naphthol (R)-(+)-1,1'-Bi-2-naphthol (R)-(+)-1,1'-Bi(2-Naphthol) [1,1'-Binaphthalene]-2,2'-Diol (R)-[1,1']-Binaphth-2-ol, (R)-BINOL (R)-(+)-1,1'-Binaphthalene-2,2'-Diol [aR,(+)]-1,1'-Binaphthalene-2,2'-diol (+)-2,2μ-Dihydroxy-1,1μ-dinaphthyl, (R)-(+)-1,1μ-Binaphthalene-2,2μ-diol, (R)-BINOL |
| CAS | 18531-94-7 |
| EINECS | 606-048-4 |
(R)-(+)-1,1'-BI-2-NAPHTHOL - Physico-chemical Properties
| Molecular Formula | C20H14O2 |
| Molar Mass | 286.32 |
| Density | 1.301 |
| Melting Point | 215-218°C |
| Boling Point | 388.69°C (rough estimate) |
| Specific Rotation(α) | 35.5 º (c=1, THF) |
| Water Solubility | Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL. |
| Solubility | dioxane: 50mg/mL, clear |
| Appearance | White crystalline powder |
| Color | white to off-white |
| Merck | 14,1226 |
| BRN | 3616837 |
| pKa | 8.29±0.50(Predicted) |
| Storage Condition | Store below +30°C. |
| Refractive Index | 36.0 ° (C=1, THF) |
| MDL | MFCD00004068 |
| Physical and Chemical Properties | Melting point 205-211°C. The specific optical rotation was 35.5 ° (c = 1, THF). |
| Use | For the synthesis of a variety of Chiral Pharmaceutical Intermediates |
(R)-(+)-1,1'-BI-2-NAPHTHOL - Risk and Safety
| Risk Codes | R25 - Toxic if swallowed R36 - Irritating to the eyes R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | DU3106100 |
| FLUKA BRAND F CODES | 10 |
| TSCA | No |
| HS Code | 29071590 |
| Hazard Class | 6.1 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 113 mg/kg |
(R)-(+)-1,1'-BI-2-NAPHTHOL - Reference Information
| Preparation | Commercially available racemic 1,1 '-bi-2-naphthol and commercially available (S)-proline are mixed in acetonitrile in a molar ratio of 1:1 (the amount of acetonitrile is 15 times the weight of racemic 1,1'-bi-2-naphthol), heated and refluxed for 3 hours, when it is cold to room temperature, white solids are precipitated, and white solids and acetonitrile filtrate are obtained by suction filtration. White solids are heated and dissolved with ethanol, naturally cooled to room temperature, let stand, and precipitate bulk colorless transparent crystals (molecular inclusion compound crystallization, Mp220-225 ℃,1HNMR(DMSO-d6):δ9.32(s,4H,disappearedafteradding D2O),7.85(d,J = 8.1Hz,8H),7.33(d,J = 9Hz,4H),7.25-7.14(m,8H),6.93(d,J = 8.1Hz,4H),3.66(t,J = 8.1Hz,1H),3.24-3.16(m,1H),3.05-2.96(m,1H),2.02-1.91(m,2H),1.80-1.66(m,2H).13CNMR(DMSO-d6):δ171.6,152.1,133.3,128.2,127.6,126.9,125.0,123.8,121.6,117.7,113.9,59.9,44.7,28.7,23.4.), suction filtration, at room temperature, the molecular inclusion compound is crystallized and added to the ethyl acetate-water two-phase system (the volume ratio of organic phase and water phase is 2:1) Stirred for 1 hour, liquid separation, aqueous phase is extracted with ether, organic phase is combined, organic phase is dried, evaporated and residue is recrystallized with toluene to obtain enantipurity (S)-1,1 '-bi-2-naphthol bulk crystal, total yield: 68%,100% ee,m.p.208-210 ℃;[α]D20 =-36.5(c1,inTHF). After the aqueous phase is evaporated and concentrated to dry, recrystallized with ethanol to recover (S)-proline, yield: 92%. acetonitrile filtrate is evaporated and concentrated to dry, the residue is extracted with ether, the ether extract is evaporated, and the evaporated residue is recrystallized twice in toluene to obtain enantiomeric R-1,1 '-bi-2-naphthol, with a total yield of 41%,100% ee,m.p.208-210 ℃;[α]D20 = +36.4(c1,inTHF). |
| Uses | Used for the synthesis of a variety of chiral pharmaceutical intermediates Used as a chiral reagent Atropine isomeric diols have many uses: in the asymmetric selective reduction of ketones The ligand in the chiral titanium catalyst is used for stereoselective reactions, such as glyoxylic acid reaction and Diels-Alder reaction; used for catalyzing the asymmetric oxidation of sulfide to sulfoxide Chiral auxiliary in the reaction; chiral lanthanide trifluoromethanesulfonic acid is generated from binaphthol, which is used as a catalyst for asymmetric Diels-Alder reactions; binaphthol derivatives have recently been found to be used in asymmetric Claisen rearrangement reactions and asymmetric epoxidation reactions; these diols (BINAP-H) lithium aluminum hydride derivatives have been widely used in the reduction reaction of ketones; chiral binaphthol salt precursors, salts used in asymmetric reactions of olefin epoxidation |
Last Update：2024-04-09 15:16:48
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