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
• UNSPSC Code: 12352005
• NACRES: NA.22
• PubChem Substance ID: 24863894
• MDL number: MFCD00145204
• Beilstein/REAXYS Number: 5279621

Properties

• Product Name: (R)-(+)-1,1′-Binaphthyl-2,2′-diamine, 99%
• 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
• SMILES string: Nc1ccc2ccccc2c1-c3c(N)ccc4ccccc34
• InChI key: DDAPSNKEOHDLKB-UHFFFAOYSA-N
• assay: 99%
• optical activity: [α]20/D +157°, c = 1 in pyridine
• optical purity: ee: 99% (HPLC)
• mp: 242-244 °C (lit.)
• Quality Level: 200

Description

Application

1,1′-Binaphthyl-2,2′-diamine derivatives have been used for asymmetric hydrogenations,[1] cyclopropanations,[2][3] and formation of chiral lactones.[3][4][5]

1,1′-Binaphthyl-2,2′-diamine derivatives have been used for asymmetric hydrogenations,[1] cyclopropanations,[2][3] and formation of chiral lactones.[3][4][5] 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.[6]

Disclaimer

May darken in storage.

General description

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine is an axially dissymmetric binaphthyl ligand mainly used in enantioselective catalysis.[6]

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: 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: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves