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| | (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate Basic information | | Reaction |
| Product Name: | (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate | | Synonyms: | Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin,4-hydroxy-, 4-oxi;(R)-5,5',6,6',7,7',8,8'-Octahydro-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate;(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate;(R)-4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide;(R)-(-)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGEN PHOSPHONATE;(R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate, (R)-(-)-BNDHP;(R)-(-)-1,1'-Biphthyl-2,2'-diyl hydrogenphosphate;(R)-1,1'-Binaphthalene-2,2'-diyl Hydrogen Phosphate,99%e.e. | | CAS: | 39648-67-4 | | MF: | C20H13O4P | | MW: | 348.29 | | EINECS: | 609-734-1 | | Product Categories: | Chiral Phosphine;Analytical Chemistry;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;Chiral Compounds;chiral;API intermediates;Chiral Compound;Chiral Phosphoric AcidsAsymmetric Synthesis;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;Chiral Resolution Reagents;Chiral Resolving Reagents;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;bc0001 | | Mol File: | 39648-67-4.mol |  |
| | (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate Chemical Properties |
| Melting point | ≥300 °C | | alpha | -607.5 º (c=1.4,MeOH) | | Boiling point | 619.5±38.0 °C(Predicted) | | density | 1.49±0.1 g/cm3(Predicted) | | refractive index | -595 ° (C=1, MeOH) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Solubility in hot Methanol, almost transparency. | | pka | 1.14±0.20(Predicted) | | form | Powder | | color | white | | Optical Rotation | [α]20/D 605°, c = 1.35 in methanol | | BRN | 4713363 | | InChI | InChI=1S/C20H13O4P/c21-25(22)23-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)24-25/h1-12H,(H,21,22) | | InChIKey | JEHUZVBIUCAMRZ-UHFFFAOYSA-N | | SMILES | O=P1(OC2C=CC3C=CC=CC=3C=2C2=C3C=CC=CC3=CC=C2O1)O | | CAS DataBase Reference | 39648-67-4(CAS DataBase Reference) |
| | (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate Usage And Synthesis |
| Reaction |
- Asymmetric hetero Diels-Alder reaction catalyzed by chiral lanthanide(III) complex.
- Highly efficient Mannich reaction.
- Acidic Resolving agent for certain amine/racemic mixtures.
| | Chemical Properties | off-white powder | | Uses | chiral ligand for hydroxycarboxylations, complexes rhodium | | Uses | The R enantiomer of binaphthol derivative as chiral quenching agent. | | Uses | A chiral ligand used in hydrocarboxylation reactions. Complexes with rhodium and mediates the asymmetric dipolar cycloaddition of diazo compounds. A number of racemic amines which have proven difficult to separate have been resolved with this chiral acid. Palladium derivatives have been used in asymmetric hydrocarboxylations, and rhodium derivatives have been used in dipolar cycloadditions. | | Purification Methods | Recrystallise it from EtOH. Reflux for 3hours in N NaOH is required to hydrolyse the cyclic phosphate. [Jacques et al. Tetrahedron Lett 4617 1971, Arnold et al. Tetrahedron 24, 343 1983.] |
| | (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate Preparation Products And Raw materials |
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