685879
(1S,2S)-1,2-Bis(2-hydroxyphenyl)ethylenediamine
95%
Synonym(s):
(1S,2S)-1,2-Bis(2-hydroxyphenyl)-1,2-ethanediamine, (S,S) Jik Chin Mother Diamine, (S,S) Diaminopharm Diamine, (S,S) Mother Diamine
About This Item
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Quality Level
Assay
95%
form
solid
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
General description
Application
- 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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Personal Protective Equipment
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Articles
Chiral vicinal diamines are of tremendous interest to the synthetic chemist as they are found in many chiral catalysts and pharmaceuticals.
Related Content
The Chin group is interested in computational and experimental approaches to understanding stereoselective recognition and catalysis. Their studies in weak forces (H-bonding, electronic and steric effects) has led to a highly efficient method for making limitless varieties of chiral vicinal diamines from the 'mother diamine' that are useful for developing stereoselective organocatalysts or transition metal-based catalysts as well as for developing drugs (Acc Chem Res (2012) p1345). The 'mother diamine' is also useful for making binol, monophos and binap analogs. The Chin group is also interested in using reversible covalent bonds for stereoselective recognition and L to D conversion of natural and non-natural amino acids (EJOC (2012) p229).
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