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685879 Sigma-Aldrich

(1S,2S)-1,2-Bis(2-hydroxyphenyl)ethylenediamine

95%

Synonym: (1S,2S)-1,2-Bis(2-hydroxyphenyl)-1,2-ethanediamine, (S,S) Jik Chin Mother Diamine, (S,S) Diaminopharm Diamine, (S,S) Mother Diamine

  • Empirical Formula (Hill Notation) C14H16N2O2

  • Molecular Weight 244.29

  •  MDL number MFCD09751761

  •  PubChem Substance ID 24885691

  •  NACRES NA.22

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Properties

Related Categories Amines, Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Chiral Catalysts, Ligands, and Reagents,
Quality Level   100
assay   95%
optical activity   [α]22/D -65°, c = 0.2 in chloroform
mp   157-162 °C
SMILES string   N[C@H]([C@@H](N)c1ccccc1O)c2ccccc2O
InChI   1S/C14H16N2O2/c15-13(9-5-1-3-7-11(9)17)14(16)10-6-2-4-8-12(10)18/h1-8,13-14,17-18H,15-16H2/t13-,14-/m0/s1
InChI key   MRNPLGLZBUDMRE-KBPBESRZSA-N

Description

General description

1,2-Bis(2-hydroxyphenyl)ethylenediamine is a chiral diamine, which acts as a key precursor (mother diamine) in the synthesis of alkyl, aryl, and heterocyclic diamines (daughter diamines), used for various synthetic applications.

Application

(1S,2S)-1,2-Bis(2-hydroxyphenyl)ethylenediamine can be used:
• As a starting material for the synthesis of Schiff base complexes of gold(III), bearing potent anticancer activity.
• As a stereoinductor in the synthesis of quinoline and isoquinoline based 1,2-diamines; that are employed as catalysts in the preparation of warfarin and coumachlor in water.

Packaging

1, 10 g in poly bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Chiral Vicinal Diamines for Asymmetric Synthesis

Chiral vicinal diamines are of tremendous interest to the synthetic chemist as they are found in many chiral catalysts and pharmaceuticals. Currently, there is no unified approach to making these chi...
ChemFiles 2007, 7.9, 7.
Keywords: Ligands, Pharmaceutical

DSM MonoPhos™ Family - Aldrich ChemFiles 2008, 8.2, 51.

Feringa and co-workers have developed a diverse array of chiral, monodentate phosphoramidites based on the privileged BINOL platform.1 The MonoPhos™ family has exhibited high levels of enantiocontrol...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 51.
Keywords: Addition reactions, Alkylations, Aminations, Annulations, Asymmetric synthesis, Catalysis, Chemfiles, Cyclizations, Desymmetrizations, Hydrogenations, Infrared spectroscopy, Ligands, Organic synthesis, Oxidations

Jik Chin Group – Products available at Aldrich from the Chin Laboratory

From our library of Articles, Sigma-Aldrich presents Jik Chin Group – Products available at Aldrich from the Chin Laboratory
Keywords: Building blocks, C-C bond formation, Catalysis, Cope Rearrangement, Ligands, Oxidations, Rearrangements, Reductions

Peer-Reviewed Papers
15

References

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