39648-67-4

Basic information

• 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'-Binaphthyl-2,2'-diyl;(R)-(-)-1,1'-Biphthyl-2,2'-diyl hydrogenphosphate
• CAS NO: 39648-67-4
• Molecular Formula: C₂₀H₁₃O₄P
• Molecular Weight: 349.3
• EINECS: -0
• Product Categories: Chiral Phosphine;Chiral Compounds;chiral;API intermediates;Analytical Chemistry;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;Chiral Compound;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Phosphoric AcidsAsymmetric Synthesis;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;Chiral Resolution Reagents;Chiral Resolving Reagents
• Mol File: 39648-67-4.mol
• Article Data: 27

Chemical Properties

• Melting Point: ≥300 °C
• Boiling Point: 619.5 °C at 760 mmHg
• Flash Point: 328.5 °C
• Appearance: white/Powder
• Density: 1.49 g/cm³
• Refractive Index: -595 ° (C=1, MeOH)
• Storage Temp.: Refrigerator
• Solubility: Solubility in hot Methanol, almost transparency.
• PKA: 1.14±0.20(Predicted)
• BRN: 4713363
• CAS DataBase Reference: (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate(39648-67-4)
• EPA Substance Registry System: (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate(39648-67-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22
• RIDADR: 3464
• WGK Germany: 3
• RTECS: RZ2475100
• F: 10-23
• Hazardous Substances Data: 39648-67-4(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 39648-67-4 differently. You can refer to the following data:
1. chiral ligand for hydroxycarboxylations, complexes rhodium
2. The R enantiomer of binaphthol derivative as chiral quenching agent.
3. 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.

Upstream product

• 124583-86-4 (R)-1,1'-binaphthalene-2,2'-diyl phosphoric acid chloride 
• 602-09-5 1,1'-bi-2-naphthol 
• 124583-86-4 (+/-)-1,1'-Binaphthyl-2,2'-diyl phosphorochloridate 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 35193-63-6 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 
• 7647-01-0 hydrogenchloride 
• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Downstream Products

• 35193-63-6 (R)-1,1'-binaphthyl-2,2'-phosphoric acid 
• 35193-63-6 (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate 
• 106463-17-6 (+)-Tamsulosin 

Relevant articles and documents

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Asymmetric ketone hydroboration catalyzed by alkali metal complexes derived from BINOL ligands

The ability of alkali metal complexes featuring functionalized BINOL-derived ligands to catalyze ketone hydroboration reactions was explored. The reduced products were formed in excellent yields and with variable enantioselectivities dependent upon the nature of the ligand and the alkali metal cation.

Diquats with Robust Chirality: Facile Resolution, Synthesis of Chiral Dyes, and Application as Selectors in Chiral Analysis

Diquats with extremely high racemization barriers with ΔG≠theor of 233 kJ mol?1 at 180 °C are described. Reported configurational robustness is due to a combination of two structural features: the rigid o-xylylene tether connecting the nitrogen atoms and the presence of two substituents in the bay region of the bipyridinium scaffold. The straightforward synthesis of diquats, plus facile resolution and derivatization make them attractive for chiral application studies. This is demonstrated by: 1) synthesis of the first non-racemic diquat dyes with pronounced chiroptical properties, and 2) capability of diquats to interact stereospecifically with chiral molecules. This suggests potential for diquat derivatives to be used as chiral selectors in separation methods.