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Merck
CN

685879

(1S,2S)-1,2-双(2-羟苯基)乙二胺

95%

别名:

(1S,2S)-1,2-双(2-羟苯基)-1,2-乙二胺

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关于此项目

经验公式（希尔记法）:
C14H16N2O2
分子量:
244.29
NACRES:
NA.22
PubChem Substance ID:
24885691
UNSPSC Code:
12352116
MDL number:
MFCD09751761

主要文件

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产品名称

(1S,2S)-1,2-双(2-羟苯基)乙二胺, 95%

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

SMILES string

N[C@H]([C@@H](N)c1ccccc1O)c2ccccc2O

InChI key

MRNPLGLZBUDMRE-KBPBESRZSA-N

assay

95%

form

solid

optical activity

[α]22/D -65°, c = 0.2 in chloroform

mp

157-162 °C

functional group

amine

Quality Level

100

相关类别

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.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

存储类别

11 - Combustible Solids

wgk

WGK 3

ppe

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

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCT9810
MKCS9009
MKCS9039
MKCV2696
MKCS2454

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Mimicking nature to make unnatural amino acids and chiral diamines
So SM, et al.
European Journal of Organic Chemistry, 2012(2), 229-241 (2012)
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)
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)
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)

商品

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.

相关内容

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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