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684031

(1S, 2S)-1,2-Bis(4-nitrophenyl)ethylenediamine dihydrochloride

Name: (1<I>S</I>, 2<I>S</I>)-1,2-Bis(4-nitrophenyl)ethylenediamine dihydrochloride
Brand: ALDRICH

97%

Synonym(s):

(1S, 2S)-1,2-Bis(4-nitrophenyl)-1,2-ethanediamine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₁₄H₁₄N₄O₄ · 2HCl

CAS Number:

1052707-07-9

Molecular Weight:

375.21

MDL number:

MFCD09836223

UNSPSC Code:

12352116

PubChem Substance ID:

329760889

NACRES:

NA.22

Assay

97%

form

powder

optical activity

[α]22/D -84.0°, c = 1 in H₂O

mp

202-207 °C

SMILES string

Cl.Cl.N[C@H]([C@@H](N)c1ccc(cc1)[N+]([O-])=O)c2ccc(cc2)[N+]([O-])=O

InChI

1S/C14H14N4O4.2ClH/c15-13(9-1-5-11(6-2-9)17(19)20)14(16)10-3-7-12(8-4-10)18(21)22;;/h1-8,13-14H,15-16H2;2*1H/t13-,14-;;/m0../s1

InChI key

PDPYGNJVCKPVGM-AXEKQOJOSA-N

Application

(1S, 2S)-1,2-Bis(4-nitrophenyl)ethylenediamine dihydrochloride can be used to prepare a fluorous Fe-salen complex, which is used as a catalyst in the asymmetric epoxidation of C-C double bonds.

Pictograms

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Unprecedented Asymmetric Epoxidation of Isolated Carbon-Carbon Double Bonds by a Chiral Fluorous Fe (III) Salen Complex: Exploiting Fluorophilic Effect for Catalyst Design

Kobayashi Y, et al.

European Journal of Organic Chemistry, 2019(13), 2401-2408 (2019)

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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