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(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate

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(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate 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'-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
  • Chiral Compounds
  • chiral
  • API intermediates
  • Synthetic Organic Chemistry
  • Chiral Compound
  • Chiral Phosphoric AcidsAsymmetric Synthesis
  • Asymmetric Synthesis
  • Chiral Catalysts, Ligands, and Reagents
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Chiral Resolution Reagents
  • Chiral Resolving Reagents
  • bc0001
Mol File:
39648-67-4.mol
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(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.
form 
Powder
pka
1.14±0.20(Predicted)
color 
white
optical activity
[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)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-20/21/22
Safety Statements 
26-36-36/37/39-22
RIDADR 
3464
WGK Germany 
3
RTECS 
RZ2475100
10-23
HS Code 
29199000

MSDS

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(R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate Usage And Synthesis

Reaction

  1. Asymmetric hetero Diels-Alder reaction catalyzed by chiral lanthanide(III) complex.
  2. Highly efficient Mannich reaction.
  3. 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 hydrogenphosphateSupplier

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