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685879

Sigma-Aldrich

(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

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About This Item

Empirical Formula (Hill Notation):
C14H16N2O2
Molecular Weight:
244.29
MDL number:
MFCD09751761
UNSPSC Code:
12352116
PubChem Substance ID:
24885691
NACRES:
NA.22

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Green asymmetric synthesis of Warfarin and Coumachlor in pure water catalyzed by quinoline-derived 1, 2-diamines
Kucherenko AS, et al.
Green Chemistry, 20(3), 754-759 (2018)
Synthesis and biological evaluation of gold (III) Schiff base complexes for the treatment of hepatocellular carcinoma through attenuating TrxR activity
Bian M, et al.
European Journal of Medicinal Chemistry, 193(36), 112234-112234 (2020)
Mimicking nature to make unnatural amino acids and chiral diamines
So SM, et al.
European Journal of Organic Chemistry, 2012(2), 229-241 (2012)
Stereospecific synthesis of C 2 symmetric diamines from the mother diamine by resonance-assisted hydrogen-bond directed diaza-Cope rearrangement.
Kim H, et al.
Journal of the American Chemical Society, 130(36), 12184-12191 (2008)

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.

Related Content

Chin Group – Professor Product Portal

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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