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685860 Sigma-Aldrich

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

95% (HPLC)

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

  • CAS Number 870991-70-1

  • Empirical Formula (Hill Notation) C14H16N2O2

  • Molecular Weight 244.29

  •  MDL number MFCD09751760

  •  PubChem Substance ID 24885846

  •  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% (HPLC)
optical activity   [α]22/D +62°, c = 1% in chloroform
mp   157-163 °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-/m1/s1
InChI key   MRNPLGLZBUDMRE-ZIAGYGMSSA-N

Description

General description

(1R, 2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine or (R, R)-1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane (HPEN) is commonly used in the stereoselective synthesis of enantiopure compounds.

Application

(1R, 2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine can be used as a precursor for the synthesis of:
• Enantiomerically pure trans-3-arylpiperazine-2-carboxylic acid derivatives via diaza-Cope rearrangement (DCR).
• 4,4′-(1,2-Diazaniumylethane-1,2-diyl)dibenzoate trihydrate by treating with terephthalaldehydic acid.

Packaging

1, 10 g in poly bottle

100 mg in glass insert

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Target organs 
Respiratory system
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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Certificate of Origin (COO)

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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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