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684147

Sigma-Aldrich

(1S, 2S)-1,2-di-1-Naphthyl-ethylenediamine dihydrochloride

97%

Synonym(s):

(S, S)-1,2-Bis(1-naphthyl)-1,2-ethanediamine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H20N2 · 2HCl
CAS Number:
1052707-27-3
Molecular Weight:
385.33
MDL number:
MFCD09836226
UNSPSC Code:
12352005
PubChem Substance ID:
329760895
NACRES:
NA.22

Quality Level

100

assay

97%

form

powder

optical activity

[α]22/D +258.0°, c = 1 in H2O

mp

219-224 °C

SMILES string

Cl[H].Cl[H].N[C@H]([C@@H](N)c1cccc2ccccc12)c3cccc4ccccc34

InChI

1S/C22H20N2.2ClH/c23-21(19-13-5-9-15-7-1-3-11-17(15)19)22(24)20-14-6-10-16-8-2-4-12-18(16)20;;/h1-14,21-22H,23-24H2;2*1H/t21-,22-;;/m0../s1

InChI key

SHNGCXWOHADIKG-IXOXMDGESA-N

Application

(1S, 2S)-1,2-di-1-Naphthyl-ethylenediamine dihydrochloride can be used to synthesize N,N′-[(1S,2S)-1,2-di-1-naphthyl-ethylene]bis2-propenamide, a chiral monomer, to prepare polymeric chiral stationary phase for HPLC.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Tharanga Payagala et al.
Analytical and bioanalytical chemistry, 399(7), 2445-2461 (2011-01-05)
Three new polymeric chiral stationary phases were synthesized based on (1S,2S)-1,2-bis(2,4,6-trimethylphenyl)ethylenediamine, (1S,2S)-1,2-bis(2-chlorophenyl)ethylenediamine, and (1S,2S)-1,2-di-1-naphthylethylenediamine via a simple free-radical-initiated polymerization in solution. These monomers are structurally related to (1S,2S)-1,2-diphenylethylenediamine which is the chiral monomer used for the commercial P-CAP-DP polymeric chiral

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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