Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

364010

Sigma-Aldrich

(1R,2R)-(+)-1,2-Diphenylethylenediamine

97%

Synonym(s):

(1R,2R)- DPEDA, (1R,2R)-DPEN, (1R,2R)-(+)-1,2-Diamino-1,2-diphenylethane

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
[C6H5CH(NH2)-]2
CAS Number:
35132-20-8
Molecular Weight:
212.29
Beilstein:
2369988
MDL number:
MFCD00082769
UNSPSC Code:
12352116
PubChem Substance ID:
24862410
NACRES:
NA.22

Quality Level

100

Assay

97%

optical activity

[α]20/D +102°, c = 1 in ethanol

optical purity

ee: 99% (GLC)

mp

79-83 °C (lit.)

SMILES string

N[C@@H]([C@H](N)c1ccccc1)c2ccccc2

InChI

1S/C14H16N2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14H,15-16H2/t13-,14-/m1/s1

InChI key

PONXTPCRRASWKW-ZIAGYGMSSA-N

Looking for similar products? Visit Product Comparison Guide

Application

General applications:
  • (1R,2R)-(+)-1,2-Diphenylethylenediamine (DPEN) is one of the widely used chiral auxiliary and ligand in the synthesis of asymmetric catalysts such as BINAP/diamine-Ru complexes for the stereoselective hydrogenation of ketones.
  • It can be used in the preparation of monosulfonyl DPEN-salt to catalyze Michael addition of various ketones to maleimides.
  • DPEN-derived chiral triazolium salts can be used to catalyze enantioselective intramolecular Stetter reaction and oxodiene Diels-Alder reaction.
  • Zinc acetate complexes of DPEDA-derived ligands can also be used to catalyze hydrosilylation of imines.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synthesis of (1 R, 2 R)-DPEN-derived triazolium salts and their application in asymmetric intramolecular Stetter reactions.
Jia M Q, et al.
Organic & Biomolecular Chemistry, 9(7), 2072-2074 (2011)
trans?[RuCl2 (phosphane) 2 (1, 2?diamine)] and Chiral trans?[RuCl2 (diphosphane)(1, 2?diamine)]: Shelf?Stable Precatalysts for the Rapid, Productive, and Stereoselective Hydrogenation of Ketones.
Doucet H, et al.
Angewandte Chemie (International Edition in English), 37(12), 1703-1707 (1998)
(1R, 2R)-DPEN-derived triazolium salts for enantioselective oxodiene Diels?Alder reactions.
Rong Z Q, et al.
Tetrahedron, 67(48), 9329-9333 (2011)
Enantioselective hydrosilylation of imines catalyzed by chiral zinc acetate complexes.
Bezlada A, et al.
The Journal of Organic Chemistry, 81(1), 336-342 (2015)
Feng Yu et al.
Chemical communications (Cambridge, England), 46(25), 4589-4591 (2010-05-21)
An unprecedented enantioselective Michael addition of various ketones to maleimides catalyzed by a simple bifunctional primary amine, monosulfonyl DPEN salt, is reported and provides the desired adducts in good to excellent yields (up to 99%) with excellent enantioselectivities (up to
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service