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685879

Sigma-Aldrich

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

95%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C14H16N2O2
Poids moléculaire :
244.29
Numéro MDL:
MFCD09751761
Code UNSPSC :
12352116
ID de substance PubChem :
24885691
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

95%

Forme

solid

Activité optique

[α]22/D -65°, c = 0.2 in chloroform

Pf

157-162 °C

Chaîne SMILES 

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

Clé InChI

MRNPLGLZBUDMRE-KBPBESRZSA-N

Description générale

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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.

Contenu apparenté

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).

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

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