134532-03-9

Basic information

• Product Name: 2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE
• Synonyms: 2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE;[1,1'-Binaphthalene]-2-ol, 2'-aMino-;2′-Amino-[1,1′-binaphthalene]-2-ol;2'-Amino-1,1'-Binaphthalen-2-Ol;2'-amino-1,1'-binaphthyl-2-ol;(+/-) -rac-2'-Amino-1,1'-binaphthalen-2-ol
• CAS NO: 134532-03-9
• Molecular Formula: C₂₀H₁₅NO
• Molecular Weight: 285.3392
• Mol File: 134532-03-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 195.5-196.5 °C (decomp)
• Boiling Point: 471.5±30.0 °C(Predicted)
• Appearance: /
• Density: 1.275±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.90±0.50(Predicted)
• CAS DataBase Reference: 2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE(134532-03-9)
• EPA Substance Registry System: 2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE(134532-03-9)

Safety Data

• Hazard Codes: Xi,N
• Statements: 41-50/53
• Safety Statements: 26-39-60-61
• Hazardous Substances Data: 134532-03-9(Hazardous Substances Data)

Usage

General Description

2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE, also known as BINAM, is a chiral molecule with two naphthyl groups connected by a bridge of two carbon atoms. It is a key intermediate in the synthesis of BINAP, a well-known chiral ligand used in asymmetric catalysis. BINAM itself has been studied for its potential applications in materials science, including as a component in chiral molecular assembly and as a precursor for the synthesis of other chiral compounds. The molecule's unique structure and properties make it a valuable tool in the field of organic chemistry and asymmetric synthesis.

Upstream product

• 602-09-5 1,1'-bi-2-naphthol 
• 74974-14-4 2,2’-bis(diphenylphosphinoamino)-1,1’-binaphthyl 
• 194-63-8 dinaphtho[2,1-b;1',2'-d]furan 
• 135-19-3 β-naphthol 
• 91-59-8 naphthalen-2-ylamine 

Downstream Products

• 194-59-2 7H-dibenzo[c,g]carbazole 
• 137848-29-4 (S)-(-)-2'-amino-[1,1'-binaphthalene]-2-ol 
• 137848-28-3 (R)-2-amino-2'-hydroxy-1,1'-binaphthyl 

Relevant articles and documents

Novel two-phase oxidative cross-coupling of the two-component molecular crystal of 2-naphthol and 2-naphthylamine

Two-phase reaction of a two-component molecular crystal of 2-naphthol and 2-naphthylamine suspended in aqueous Fe3+ solutions gives a cross-coupling product, 2-amino-2′-hydroxy-1,1′-binaphthalene, with good selectivity.

A general and facile approach for the synthesis of 2'-functionalized 1,1'-binapthyl-2-ols

A facile and efficient protocol for the synthesis of 2'-functionalized 1,1'-binaphthyl-2-ols has been developed. The C,O-dilithio reagent (2) generated by the reductive ring-opening of binaphthofuran (1) with lithium was treated with the corresponding electrophiles to give 2'-functionalized 1,1'-binaphthyl-2-ols including the halides (3), amine (4), acid (5), aldehyde (6), carbonate (7) or phosphonate (8), respectively, in moderate to good yields.

A practical synthesis of 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN)

A practical synthesis of 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) was realized from BINOL through a single step. Its facile purification procedure makes the process amenable for large scale synthesis of NOBIN.

Method for resolving chiral compound

The invention relates to the field of organic chemistry, and in particular, relates to a method for resolving a chiral compound. The method for resolving the chiral compound provided by the inventioncomprises the step of carrying out addition reaction on

Isothiourea-Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols

An operationally simple isothiourea-catalysed acylative kinetic resolution of unprotected 1,1′-biaryl-2,2′-diol derivatives has been developed to allow access to axially chiral compounds in highly enantioenriched form (s values up to 190). Investigation of the reaction scope and limitations provided three key observations: i) the diol motif of the substrate was essential for good conversion and high s values; ii) the use of an α,α-disubstituted mixed anhydride (2,2-diphenylacetic pivalic anhydride) was critical to minimize diacylation and give high selectivity; iii) the presence of substituents in the 3,3′-positions of the diol hindered effective acylation. This final observation was exploited for the highly regioselective acylative kinetic resolution of unsymmetrical biaryl diol substrates bearing a single 3-substituent. Based on the key observations identified, acylation transition state models have been proposed to explain the atropselectivity of this kinetic resolution.