382426

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine

99%

• Synonym(s): (R)-(+)-1,1′-Bi(2-naphthylamine), (R)-(+)-1,1′-Binaphthalene-2,2′-diamine, (R)-(+)-2,2′-Diamino-1,1′-binaphthalene, (R)-(+)-DABN
• Linear Formula: H₂NC₁₀H₆C₁₀H₆NH₂
• CAS Number: 18741-85-0
• Molecular Weight: 284.35
• Beilstein: 5279621
• MDL number: MFCD00145204
• UNSPSC Code: 12352005
• PubChem Substance ID: 24863894
• NACRES: NA.22

Properties

• 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.

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.

Caution

May darken in storage.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves