137848-28-3

Basic information

• Product Name: (R)-NOBIN
• Synonyms: S-(-)-2-AMINO-2'-HYDROXY-1,1'-BINAPHTYL;(S)-(-)-2-AMINO-2'-HYDROXY-1,2'-BINAPHTHYL;(R)-(+)-NOBIN;R-NOBIN;R-(+)-2-AMINO-2'-HYDROXY-1,1'-BINAPHTYL;(R)-(+)-2-AMINO-2'-HYDROXY-1,1'-BINAPHTHYL;R-2'-AMINO-1,1'-BINAPHTHALEN-2-OL;(R)-(+)-2-AMINO-2'-HYDROXY-1 1'-BINAPHT
• CAS NO: 137848-28-3
• Molecular Formula: C₂₀H₁₅NO
• Molecular Weight: 285.34
• Product Categories: chiral;CHIRAL COMPOUNDS;Chiral Compound;Auxiliaries,Catalysts
• Mol File: 137848-28-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 171.0 to 175.0 °C
• Boiling Point: 471.5 ºC at 760 mmHg
• Appearance: /
• Density: 1.275 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.90±0.50(Predicted)
• CAS DataBase Reference: (R)-NOBIN(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-NOBIN(137848-28-3)
• EPA Substance Registry System: (R)-NOBIN(137848-28-3)

Safety Data

• Hazard Codes: Xi,N
• Statements: 41-50/53
• Safety Statements: 26-39-60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 137848-28-3(Hazardous Substances Data)

Usage

Description

(R)-NOBIN, also known as (R)-(+)-2′-Amino-1,1′-binaphthalen-2-ol, is a non-symmetrically substituted 1,1′-binaphthalene ligand. It is characterized by its red crystal appearance and is known for its unique chemical properties that make it a valuable compound in various applications.

Uses

Used in Asymmetric Synthesis:
(R)-NOBIN is used as a catalyst in the asymmetric phase-transfer catalysis (PTC) synthesis of α-amino acids. Its chiral nature allows for the selective formation of specific enantiomers, which is crucial in the production of biologically active compounds and pharmaceuticals.
Used in Polymer Science:
(R)-NOBIN is used as a reactant in the formation of poly(ester-amide)s when it reacts with trans-azobenzene-4,4′-dicarbonyl chloride. These polymers exhibit a backbone light-regulated chiroptical response, making them potentially useful in the development of advanced materials with applications in optics, sensors, and other technology-driven fields.
Used in Chemical Research:
Due to its unique structure and properties, (R)-NOBIN is also used in chemical research to study the effects of chirality on reaction mechanisms, catalysis, and the development of new synthetic methods. This contributes to the broader understanding of organic chemistry and the design of novel molecules with specific functions.
Used in Pharmaceutical Industry:
(R)-NOBIN's potential applications in the pharmaceutical industry are vast, as its chiral nature can be exploited to develop new drugs with improved efficacy and selectivity. The compound can be used in the synthesis of enantiomerically pure drug candidates, which is essential for ensuring the desired therapeutic effects and minimizing side effects.

Upstream product

• 425687-39-4 (+/-)-2-amino-2'-methoxy-1,1'-binaphthyl 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 32316-92-0 naphthalene-2-boronic acid 
• 91-59-8 naphthalen-2-ylamine 
• 135-19-3 β-naphthol 
• 602-09-5 1,1'-bi-2-naphthol 
• 194-63-8 dinaphtho[2,1-b;1',2'-d]furan 
• 74974-14-4 2,2’-bis(diphenylphosphinoamino)-1,1’-binaphthyl 
• 2449-05-0 dibenzyl azodicarboxylate 
• 134532-03-9 2-amino-2’-hydroxy-1,1’-binaphthyl 

Downstream Products

• 137848-29-4 (S)-(-)-2'-amino-[1,1'-binaphthalene]-2-ol 

Relevant articles and documents

Tandem approach to NOBIN analogues from arylhydroxylamines and diaryliodonium salts: via [3,3]-sigmatropic rearrangement

Herein, we present a transition-metal free direct O-arylation of arylhydroxylamines employing diaryliodonium salts as arylation reagents to form transient N,O-diarylhydroxylamines that could subsequently undergo [3,3]-sigmatropic rearrangement and re-aromatization to afford structurally diverse NOBIN analogs in good to excellent yields under mild conditions.

Synthesis and resolution of racemic 2-amino-2′-hydroxy-1,1′-binaphthyl

The title compound 3 has been prepared via a highly selective, Cu(II)-mediated cross-coupling of 2-aminonaphthalene 1 and 2-naphthol 2 and resolved into enantiomers via crystallization of diastereoisomeric salts with (1S)-(+)-10-camphorsulfonic acid. The method has been optimized and the use of chromatography eliminated.

Synthesis of Enantiomerically Pure 2,2'-Dihydroxy-1,1'-binaphthyl, 2,2'-Diamino-1,1'-binaphthyl, and 2-Amino-2'-hydroxy-1,1'-binaphthyl. Comparison of Processes Operating as Diastereoselective Crystallization and as Second-Order Asymmetric Transformation

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Kinetic resolution of axially chiral 2-amino-1,1′-biaryls by phase-transfer-catalyzed N-allylation

Going through a phase: The highly selective kinetic resolution of the title compounds, which are important chiral building blocks, was achieved by phase-transfer-catalyzed N-allylation. This synthetic method was applied to the highly enantioselective desymmetrization of a biaryl compound. Copyright

Kinetic resolution of 1,1-biaryl-2,2-diols and amino alcohols through NHC-catalyzed atroposelective acylation

We present here a highly efficient NHC-catalyzed kinetic resolution of a wide range of 1,1-biaryl-2,2-diols and amino alcohols to provide them in uniformly ≥99% ee. This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.

Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases

Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative

Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction

A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.