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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

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Chiral Phosphoric Acids
Quality Level   100
assay   95%
optical activity   [α]20/D -220°, c = 1 in chloroform (typical)
mp   162-175 °C
SMILES string   OP1(=O)Oc2c(cc3ccccc3c2-c4c(O1)c(cc5ccccc45)-c6cc(cc(c6)C(F)(F)F)C(F)(F)F)-c7cc(cc(c7)C(F)(F)F)C(F)(F)F
InChI   1S/C36H17F12O4P/c37-33(38,39)21-9-19(10-22(15-21)34(40,41)42)27-13-17-5-1-3-7-25(17)29-30-26-8-4-2-6-18(26)14-28(32(30)52-53(49,50)51-31(27)29)20-11-23(35(43,44)45)16-24(12-20)36(46,47)48/h1-16H,(H,49,50)
InChI key   DQORDVSQWPKAQJ-UHFFFAOYSA-N

Description

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]

Packaging

100 mg in clear glass bottle

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
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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