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| | (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL Basic information | | Reaction |
| Product Name: | (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL | | Synonyms: | (R)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAP&;(R)-(+)-2,2'-Bis(methoxymethoxy)-1,1'-binaphthyl,98%;2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHALENE;(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHALENE;(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;(S)-(-)-2,2'-BIS(METHOXYMETHOXY)-1,1-BINAPHTHALENE;(S)-(-)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL;(S)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL | | CAS: | 173831-50-0 | | MF: | C24H22O4 | | MW: | 374.43 | | EINECS: | | | Product Categories: | BINOL Series;Chiral Oxygen;BINOLs;Chiral Catalysts, Ligands, and Reagents;Privileged Ligands and Complexes;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Other Ligands;Catalysis and Inorganic Chemistry;Chemical Synthesis | | Mol File: | 173831-50-0.mol |  |
| | (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL Chemical Properties |
| Melting point | 92-96 °C(lit.) | | alpha | +85° (c 0.22, CHCl3) | | Boiling point | 477.8±45.0 °C(Predicted) | | density | 1.182±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | soluble in Toluene | | form | Powder | | color | white | | Optical Rotation | [α]20/D +92°, c = 1% in chloroform | | InChI | 1S/C24H22O4/c1-25-15-27-21-13-11-17-7-3-5-9-19(17)23(21)24-20-10-6-4-8-18(20)12-14-22(24)28-16-26-2/h3-14H,15-16H2,1-2H3 | | InChIKey | YIAQRNNJNMLGTP-UHFFFAOYSA-N | | SMILES | COCOc1ccc2ccccc2c1-c3c(OCOC)ccc4ccccc34 |
| Hazard Codes | Xi,N | | Risk Statements | 41-50/53 | | Safety Statements | 26-39-60-61-36/39-25 | | RIDADR | UN 3077 9/PG 3 | | WGK Germany | 3 | | HS Code | 29093090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Acute 1
Aquatic Chronic 1
Eye Dam. 1 |
| | (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL Usage And Synthesis |
| Reaction | Starting material for the preparation of a variety of 3,3'-substituted binaphthols.
| | Chemical Properties | Colorless solid | | Uses | An intermediate in the symmetric synthesis of BINOL-terpyridine ligands. | | Uses | 3- or 3,3′-di-substituted products can be obtained easily via ortho-metallation and subsequent treatment with an electrophile to give the corresponding BINOL derivatives. | | Synthesis | Sodium hydride (NaH, 1.92 g, 80 mmol) was slowly added to N,N-dimethylformamide (DMF, 30 mL) under ice bath conditions. Subsequently, a tetrahydrofuran (THF, 50 mL) solution of 1,1'-bi-2-naphthol (BINOL, 10 g, 34 mmol) was added slowly dropwise to the above mixture for 20 min. after 30 min, chloromethyl methyl ether (6.4 g, 80 mmol) was added slowly dropwise for the same period of time. The reaction process was monitored by thin layer chromatography (TLC). The reaction mixture was extracted with chloroform and water after stirring for 1 h. The organic layer was separated to obtain the crude product. The crude product was further purified by silica gel column chromatography with petroleum ether/ethyl acetate (5:1, v/v) as eluent. Finally, (R)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl was obtained in 90% yield. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.95-7.93 (d, J = 9.6 Hz, 2H), 7.87-7.85 (d, J = 8.4 Hz, 2H), 7.58-7.56 (d, J = 9.6 Hz, 2H), 7.35-7.31 (m, 2H), 7.23-7.14 (m, 4H ), 5.08-4.96 (q, J = 6.8 Hz, 4H), 3.13 (s, 6H). | | References | [1] Organic Letters, 2004, vol. 6, # 16, p. 2701 - 2704
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 19, p. 2161 - 2166
[3] Chemistry - A European Journal, 2018, vol. 24, # 48, p. 12607 - 12612
[4] Chemistry Letters, 1995, # 12, p. 1113 - 1114
[5] Organic Preparations and Procedures International, 1995, vol. 27, # 6, p. 685 - 690 |
| | (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL Preparation Products And Raw materials |
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