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

Description

(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is a chiral binaphthyl derivative that exists as an off-white powder. It is known for its ability to form complexes with rhodium and is utilized as a chiral ligand in various chemical reactions, including hydroxycarboxylations and hydrocarboxylations. (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate has also been effective in resolving racemic amines that are difficult to separate and has found applications in the asymmetric synthesis of various compounds.

Uses

Used in Chemical Synthesis:
(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used as a chiral ligand for hydroxycarboxylations and hydrocarboxylations, facilitating the formation of complex molecules with high enantioselectivity and efficiency.
Used in Pharmaceutical Industry:
(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used as a chiral quenching agent in the pharmaceutical industry, aiding in the separation and resolution of racemic amines that are challenging to isolate.
Used in Catalyst Development:
In the field of catalysis, (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used to form complexes with rhodium, which are then employed in asymmetric dipolar cycloadditions of diazo compounds. This application has led to the development of novel catalysts for various chemical reactions.
Used in Asymmetric Synthesis:
(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used as a chiral ligand in asymmetric synthesis, enabling the production of enantiomerically pure compounds with high selectivity. This is particularly important in the synthesis of pharmaceuticals and agrochemicals, where the stereochemistry of the molecule can significantly impact its biological activity.
Used in Research and Development:
In the research and development sector, (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used to study the properties and reactivity of chiral ligands, as well as to develop new methods for asymmetric catalysis and synthesis. (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate has proven valuable in advancing the understanding of chiral chemistry and its applications in various industries.

Reaction

Asymmetric hetero Diels-Alder reaction catalyzed by chiral lanthanide(III) complex. Highly efficient Mannich reaction. Acidic Resolving agent for certain amine/racemic mixtures.

Upstream product

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

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

FUSED RING PYRIMIDONE DERIVATIVES FOR USE IN THE TREATMENT OF HBV INFECTION OR OF HBV-INDUCED DISEASES

Provided are compounds according to any of Formula (I-1) to (I-7), pharmaceutical compositions comprising at least one of said compounds, their use as a medicament, and their use in treating chronic hepatitis B virus (HBV) infection. Methods for preparing compounds according to any of Formula (I-1) to (I-7) are also provided.

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.