746-46-3

Basic information

• Product Name: (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid
• CAS NO: 746-46-3
• Molecular Weight: 342.351
• Mol File: 746-46-3.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid(746-46-3)
• EPA Substance Registry System: (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid(746-46-3)

Safety Data

• Hazardous Substances Data: 746-46-3(Hazardous Substances Data)

Upstream product

• 18531-96-9 1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 129207-26-7 (R)-1,1'-Binaphthalene-2-carbonitrile-2'-carbonyl chloride 
• 121314-72-5 (R)-1,1’-binaphthl-2,2’-dicarbaldehyde 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 
• 86457-66-1 rac-2,2'-Binaphthyldicarboxylic acid dichloride 
• 78038-79-6 (+/-)-2,2'-bis(hydroxymethyl)-1,1'-binaphthyl 
• 89555-39-5 methyl 1-bromo-2-naphthalenecarboxylate 
• 20717-79-7 1-bromo-2-naphthoic acid 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 596107-65-2 C₄₂H₃₈N₂O₄ 
• 596107-64-1 C₃₄H₂₂N₂O₄ 

Downstream Products

• 641-13-4 anthanthrone 
• 881812-14-2 (R,R,RS)-2,6-bis(2-biphenyl)-4-methyl-4,5-dihydro-3H-4-azacyclohepta[2,1-a;3,4a']dinaphthalene 
• 881812-20-0 4-methyl-2,6-bis-(2-phenyl-naphthalen-1-yl)-4,5-dihydro-3H-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 881812-36-8 2,6-bis-[2,4-bis-(4-trifluoromethyl-phenyl)-naphthalen-1-yl]-4-methyl-4,5-dihydro-3H-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 1330180-23-8 C₃₆H₂₆O₄Si₂ 

Relevant articles and documents

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.

Practical synthetic protocols of enantiopure 1,1′-binaphthyl-2, 2′-dicarboxylic acid and 2,2′-dicyano-1,1′-binaphthyl starting from optically active dibromide precursor

Dilithiation of optically active 2,2′-dibromo-1,1 ′-binaphthyl 2 with t-BuLi followed by carboxylation of the resulting dilithio-intermediate 3 with CO2 gave optically active 1,1′-binaphthyl-2,2′-dicarboxylic acid 1, which was further transformed to its dicyano derivative 4. Both of these transformations were carried out in a one-pot operation and the products were obtained in excellent yields with no observable racemization.

A novel axially chiral 2,2′-bipyridine N,N′-dioxide. Its preparation and use for asymmetric allylation of aldehydes with allyl(trichloro)silane as a highly efficient catalyst

(Matrix presented) New axially chiral 2,2′-bipyridine N,N′-dioxides were obtained by a new method that does not involve any procedures for the separation of enantiomers. One of the dioxides, (R)-3,3′-bis(hydroxymethyl)-6,6′-diphenyl-2,2′-bipyridine N,N′-dioxide, exhibited extremely high catalytic activity for the asymmetric allylation of aldehydes with allyl(trichloro)silane. The allylation of aromatic aldehydes proceeded in the presence of 0.01 or 0.1 mol % of the dioxide catalyst to give the corresponding homoallyl alcohols of up to 98% ee.