24161-30-6

Basic information

• Product Name: [aR,(-)]-1,1'-Binaphthalene
• Synonyms: [aR,(-)]-1,1'-Binaphthalene
• CAS NO: 24161-30-6
• Molecular Formula: C₂₀H₁₄
• Molecular Weight: 254.32516
• Mol File: 24161-30-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [aR,(-)]-1,1'-Binaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: [aR,(-)]-1,1'-Binaphthalene(24161-30-6)
• EPA Substance Registry System: [aR,(-)]-1,1'-Binaphthalene(24161-30-6)

Safety Data

• Hazardous Substances Data: 24161-30-6(Hazardous Substances Data)

Usage

Purification Methods

Purify 1,1’-binaphthyl through a silica gel column with Me2CO/*C6H6 [or Al2O3 with 10% *C6H6/pet ether (b 30-60o)] and recrystallise it from EtOH, pentane, or slow evaporation of *C6H6, Me2CO or Et2O solutions. Half life ~10hours at 25o in various solvents. [Wilson & Pincock J Am Chem Soc 97 1474 1975, Akimoto & Yamada Tetrahedron 27 5999 1971, Beilstein 5 I 358, 5 II 642, 5 III 2465, 5 IV 2634.]

Upstream product

• 4004-51-7 tri-1-naphthyl phosphate 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 
• 90-11-9 1-Bromonaphthalene 
• 13922-41-3 1-Naphthylboronic acid 

Downstream Products

• 1186392-43-7 2-methyl-1,2,3,4-tetrahydroquinoline phosphoramidite 
• 604-53-5 1,1'-bisnaphthalene 

Relevant articles and documents

Synthesis of 1,1′-binaphthyl derivatives by Miyaura-Suzuki cross-coupling in cholesteric liquid crystal phase

We synthesized 1,1′-binaphthyl and 2-substituted-1,1′- binaphthyl by the Miyaura-Suzuki cross-coupling reaction in cholesteric liquid crystal (CLC) media. The1H and13C NMR and UV-Vis absorption spectra of the compounds thus prepared were examined. The liquid crystallinity of the CLC media before and after the reaction was confirmed by differential scanning calorimetry, polarizing optical microscopy, and visual contact in order to characterize the reaction in a CLC phase.

Synthesis and catalytic activity of chiral linker-bridged bis-N-heterocyclic carbene dipalladium complexes

A series of new chiral-bridged N-heterocyclic carbene ligands with different substituents and their corresponding palladium complexes have been synthesised. The effect of the substituents on the catalytic activity of these Pd complexes was investigated in the Suzuki reaction of p-bromotoluene with phenylboronic acid, and the results showed that the complexes with aryl substituents performed better than those with alkyl substituents. The complex with the most sterically hindered substituent (diisopropyl on a phenyl group) performed best, and it was also an efficient catalyst for the reaction of various arylboronic acids with aryl halides having different electronic and steric properties. In addition, it was employed as a catalyst in the asymmetric Suzuki reaction, but only moderate yields of 1,1-binaphthalenes with less than 20% enantiomeric excess were obtained.

Synthesis and characterization of novel chiral NHC-palladium complexes and their application in copper-free Sonogashira reactions

A new series of chiral N-heterocyclic carbene (NHC) palladium complexes were synthesized from a relatively inexpensive amino acid, l-phenylalanine. All these compounds were fully characterized by 1H-NMR, 13C-NMR and elemental analysis. The X-ray molecular structures of two of the complexes were reported. The catalytic activity of the four palladium complexes was successfully tested in the Sonogashira reaction under copper free conditions in air. The palladium complex 3a provided good activity in the Sonogashira coupling reaction. The Royal Society of Chemistry 2012.

Asymmetric hydrogenation of aromatic ketones with new P-chirogenic monophosphine ligands

Novel P-chirogenic anisylphenyl-HMOP derivatives have been synthesised from (R)-2,2′-bis-(trifluoromethanesulfonyloxy)1,1′-binaphthyl. Preliminary results concerning the asymmetric hydrogenation of acetophenone and 3,5-bis(trifluoromethyl)acetophenone with Ru(II)-HMOP complexes in combination with various diamines was also tackled.

Photoinduced electron-transfer reactions of tri-1-naphthyl phosphate and di-1-naphthyl methylphosphonate sensitised by 9,10-dicyanoanthracene

1,1′-Binaphthyl is formed by photoinduced electron-transfer reactions of tri-1-naphthyl phosphate and di-1-naphthyl methylphosphonate sensitised by 9,10-dicyanoanthracene in MeCN, while no reaction occurs in the case of mono-1-naphthyl and di- or tri-phenyl esters.

Stereospecific functionalization of (R)-(-)-1,1'-BI-2-naphthol triflate

Several examples of transition metal mediated functionalization of chiral 1,1'-bi-2-naphthol triflate are described which proceed with complete retention of substrate chirality. The transformation described demonstrate the potential of Pd(0) mediated reactions for the stereoselective transformation of the C-O bonds in this substrate.