137848-29-4

Basic information

• Product Name: (S)-2'-Amino-1,1'-binaphthalen-2-ol
• Synonyms: (S)-(-)-2-AMINO-2'-HYDROXY-1 1'-BINAPHT;S)-(-)-2-Amino-2'-Hydroxy-1,1'-Binaphthol;(S)-(+)-2-AMINO-2''-HYDROXY-1,1''-BINAPHTHYL / S-NOBIN;(S)-(-)-NOBIN 99%;S-2'-Amino-1,1'-binaphthalen-2-ol, S-NOBIN;1-(2-aMinonaphthalen-1-yl)naphthalen-2-ol;(S)-(-)-1-(2-Amino-1-naphthyl)-2-naphthol (S)-(-)-NOBIN (S)-(-)-2'-Amino-1,1'-binaphthalen-2-ol;(S)-(-)-2-Amino-2'-hydroxy-1,1'-binaphthalene
• CAS NO: 137848-29-4
• Molecular Formula: C₂₀H₁₅NO
• Molecular Weight: 285.34
• Product Categories: chiral;CHIRAL COMPOUNDS;Auxiliaries,Catalysts
• Mol File: 137848-29-4.mol
• Article Data: 38

Chemical Properties

• Melting Point: 171.0 to 175.0 °C
• Boiling Point: 471.5 °C at 760 mmHg
• Flash Point: 239 °C
• Appearance: /
• Density: 1.275
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.90±0.50(Predicted)
• CAS DataBase Reference: (S)-2'-Amino-1,1'-binaphthalen-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2'-Amino-1,1'-binaphthalen-2-ol(137848-29-4)
• EPA Substance Registry System: (S)-2'-Amino-1,1'-binaphthalen-2-ol(137848-29-4)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53-41
• Safety Statements: 26-36/37/39-61-60-39
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 137848-29-4(Hazardous Substances Data)

Usage

Description

(S)-2'-Amino-1,1'-binaphthalen-2-ol, also known as (S)-NOBIN, is a non-symmetrically substituted 1,1'-binaphthalene ligand characterized by its red crystalline appearance. It is a versatile compound with significant applications in the field of organic chemistry, particularly in asymmetric synthesis and the preparation of various analogs.

Uses

Used in Asymmetric Synthesis:
(S)-2'-Amino-1,1'-binaphthalen-2-ol is used as a catalyst in the asymmetric synthesis of unnatural α-alkyl amino acids by phase-transfer catalysis (PTC). Its unique structure and properties enable the selective formation of desired enantiomers, which are crucial in the development of pharmaceuticals and agrochemicals.
Used in Catalyst Preparation:
(S)-NOBIN serves as a starting material for the preparation of N-monoalkyl and N,N-dialkyl (S)-NOBIN analogs. These analogs are synthesized by reacting (S)-NOBIN with aldehydes through a reductive amination reaction, further expanding the range of applications for this versatile ligand.
Used in Hartwig-Buchwald Arylation:
(S)-2'-Amino-1,1'-binaphthalen-2-ol is also utilized in the Hartwig-Buchwald arylation reaction to obtain N-monoaryl derivatives. This reaction is an important method for the formation of carbon-carbon and carbon-heteroatom bonds, which are essential in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Chemical Research:
As a red crystalline compound with unique chemical properties, (S)-2'-Amino-1,1'-binaphthalen-2-ol is valuable in chemical research for understanding the behavior of binaphthalene ligands and their potential applications in various chemical processes.

Upstream product

• 91-59-8 naphthalen-2-ylamine 
• 135-19-3 β-naphthol 
• 134532-03-9 2-amino-2’-hydroxy-1,1’-binaphthyl 
• 6039-59-4 methyl 1-methoxy-2-naphthoate 
• 129656-73-1 (-)-menthyl 1-(-)-menthyloxy-2-naphthoate 
• 116741-64-1 (-)-menthyl (S)-2'-methoxy-1,1'binaphthalene-2-carboxylate 
• 80317-69-7 (aS)-2’-methoxy-(1,1’-binaphthyl)-2-carboxylic acid 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Relevant articles and documents

Synthesis of new BINAP-based aminophosphines and their 31P-NMR spectroscopy

BINAP aminophosphines are prevalent N,P-bidentate, chiral ligands for asymmetric catalysis. While modification via the BINAP-nitrogen linkage is well explored and has provided a diverse body of derivatives, modification of the other substituents of the phosphorous center is another avenue in generating new congeners of this important class of chiral ligands. Herein reported are new BINAP aryl aminophosphines with electron rich or deficient substituents on the aryl rings. This scalable synthesis converted readily available starting material, (S)-BINOL, to a key intermediate (S)-NOBIN, from which the final chiral aminophosphines were prepared via a palladium-catalyzed, phosphonylation reaction. The aryl substituents are able to modify the electronic properties of the phosphorous center as indicated by the range of 31P-NMR shifts of these new ligands. A computational analysis was performed to linearly quantitate contributions to the 31P-NMR shifts from both resonance and field effects of the substituents. This correlation may be useful for designing and preparing other related aminophosphines with varying ligand properties.

Synthesis and optical properties of (S)-Nobin

A preparative method of synthesis of optically pure S-2-amino-2'-hydroxy-1, 1'-binaphthyl (S-Nobin), the precoursor in the synthesis of other asymmetric 1,1-binaphthyls applied as the ligands at the creation of the catalysts of asymmetric synthesis, is mo

Enantioselective catalysis. Part 143: Astonishingly high enantioselectivity in the transfer hydrogenation of acetophenone with 2-propanol using Ru complexes of the Schiff base derived from (S)-2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) and 2-pyridinecarbaldehyde

A series of bidentate and tridentate (S)-NOBIN derivatives was synthesised and tested as chiral ligands in the Ru-catalysed enantioselective transfer hydrogenation of acetophenone with 2-propanol. Despite the similarities in chemical structure, only the imine derived from (S)-NOBIN and 2-pyridinecarbaldehyde and the corresponding amine (obtained by NaBH4 reduction of the imine) afforded (S)-1-phenylethanol in nearly quantitative yields and outstanding enantioselectivities of up to 97% e.e.

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.