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(S)-(-)-2-Amino-2'-hydroxy-1,1'-binaphthyl

(S)-(-)-2-Amino-2'-hydroxy-1,1'-binaphthyl

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Catalog Number

ACM137848294-2

Product Name

Structure

CAS

137848-29-4

Product Overview
Usage

IUPAC Name

1-(2-aminonaphthalen-1-yl)naphthalen-2-ol;

Molecular Weight

285.346g/mol

Molecular Formula

C20H15NO;

Canonical SMILES

C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)O)N;

InChI

InChI=1S/C20H15NO/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,22H,21H2;

InChI Key

HIXQCPGXQVQHJP-UHFFFAOYSA-N;

Complexity

384

Covalently-Bonded Unit Count

Exact Mass

285.115g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

285.115g/mol

Rotatable Bond Count

Topological Polar Surface Area

46.2A^2

Application

The purpose of (S)-(-)-2-Amino-2'-hydroxy-1,1'-binaphthyl is to serve as a versatile catalyst and starting material in organic synthesis. This non-symmetrically substituted 1,1'-binaphthalene ligand is primarily used as a catalyst for phase-transfer catalysis, aiding in the asymmetric synthesis of unnatural α-alkyl amino acids. Additionally, it acts as a foundational compound for synthesizing various analogs. Through reductive amination reactions with aldehydes, it facilitates the creation of N-monoalkyl and N,N-dialkyl analogs. Furthermore, it enables the synthesis of N-monoaryl derivatives through the Hartwig-Buchwald arylation reaction, making it an invaluable component in advanced chemical synthesis applications.

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