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248932 Sigma-Aldrich

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate

≥98%

Synonym: (R)-(−)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate, (R)-4-Hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide

  • CAS Number 39648-67-4

  • Empirical Formula (Hill Notation) C20H13O4P

  • Molecular Weight 348.29

  •  Beilstein Registry Number 4713363

  •  MDL number MFCD00010045

  •  PubChem Substance ID 24854961

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Chiral Phosphoric Acids, Chiral Resolution Reagents,
InChI Key   JEHUZVBIUCAMRZ-UHFFFAOYSA-N
assay   ≥98%
optical activity   [α]20/D −605°, c = 1.35 in methanol

Description

Packaging

1, 5 g in glass bottle

Application

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.

Used in a chiral Bronsted acid catalyzed enantoselective Mannich reaction.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

HPLC Analysis of 1,1'-Binaphthyl-2,2'-diyl Hydrogenphosphate Enantiomers on Astec® (R,R) P-CAP™

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of 1,1'-Binaphthyl-2,2'-diyl Hydrogenphosphate Enantiomers on Astec® (R,R) P-CAP™
Keywords: Chromatography, High performance liquid chromatography

Peer-Reviewed Papers
15

References

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