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  • 674605 - (R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate

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674605 Sigma-Aldrich

(R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate

95%

Synonym: (11bR)-2,6-Bis[3,5-bis(trifluoromethyl)phenyl]-4-hydroxydinaphtho[2,1-d:1′,2′-f]-1,3,2-dioxaphosphepin 4-oxide, (R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-bi-2-naphthol cyclic monophosphate

  • CAS Number 791616-62-1

  • Empirical Formula (Hill Notation) C36H17F12O4P

  • Molecular Weight 772.47

  •  PubChem Substance ID 24885225

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Chiral Phosphoric Acids
InChI Key   DQORDVSQWPKAQJ-UHFFFAOYSA-N
assay   95%
optical activity   [α]20/D -220°, c = 1 in chloroform (typical)
mp   162-175 °C

Description

Application

As a chiral Bronsted acid, BINOL- derived cyclic phosphoric acid (such as Akiyama chiral Bronsted acid) was also shown to be an efficient catalyst for the hydrophosphonylation of aldimines at room temperature.

Packaging

100 mg in clear glass bottle

General description

(R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate is a BINOL-based chiral phosphoric acid, which can efficiently catalyze the nucleophilic addition to imine substrates. [BINOL=1,1′-bi-2-naphthol]

Safety & Documentation

Safety Information

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

Articles

Chiral Phosphoric Acids

BINOL-derived phosphoric acids are capable of catalyzing a range of interesting processes of which nucleophilic addition reactions to imine substrates are particularly noteworthy. List and coworkers ...
Aldrich ChemFiles 2007, 7.9, 11.
Keywords: Addition reactions, Aminations, Asymmetric synthesis, Catalysis, Chemfiles, Diels-Alder reaction, Nucleophilic additions, Pictet-Spengler reaction, Reductions, Reductive aminations

Peer-Reviewed Papers
15

References

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