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382426 Sigma-Aldrich

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine

99%

Synonym: (R)-(+)-1,1′-Bi(2-naphthylamine), (R)-(+)-1,1′-Binaphthalene-2,2′-diamine, (R)-(+)-2,2′-Diamino-1,1′-binaphthalene, (R)-(+)-DABN

  • CAS Number 18741-85-0

  • Linear Formula H2NC10H6C10H6NH2

  • Molecular Weight 284.35

  •  Beilstein/REAXYS Number 5279621

  •  MDL number MFCD00145204

  •  PubChem Substance ID 24863894

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Other Chiral Ligands
Quality Level   200
assay   99%
optical activity   [α]20/D +157°, c = 1 in pyridine
optical purity   ee: 99% (HPLC)
mp   242-244 °C (lit.)
SMILES string   Nc1ccc2ccccc2c1-c3c(N)ccc4ccccc34
InChI   1S/C20H16N2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12H,21-22H2
InChI key   DDAPSNKEOHDLKB-UHFFFAOYSA-N

Description

General description

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine is an axially dissymmetric binaphthyl ligand mainly used in enantioselective catalysis.

Application

1,1′-Binaphthyl-2,2′-diamine derivatives have been used for asymmetric hydrogenations, cyclopropanations, and formation of chiral lactones. Its chiral sulphonamide, chiral diphenylphosphoramide and chiral diphenylthiophosphoramide derivatives are useful ligands for asymmetric addition reaction of diethylzinc to aldehydes in the presence of titanium(IV) alkoxide.

1,1′-Binaphthyl-2,2′-diamine derivatives have been used for asymmetric hydrogenations, cyclopropanations, and formation of chiral lactones.

Packaging

1 g in glass bottle

Caution

May darken in storage.

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
Peer-Reviewed Papers
15

References

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