Skip to Content
Merck
All Photos(2)

Key Documents

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


About This Item

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

Quality Level

Assay

97%

optical activity

[α]20/D +102°, c = 1 in ethanol

optical purity

ee: 99% (GLC)

mp

79-83 °C (lit.)

functional group

amine
phenyl

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

Signal Word

Warning

Hazard Statements

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

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)
(1R, 2R)-DPEN-derived triazolium salts for enantioselective oxodiene Diels?Alder reactions.
Rong Z Q, et al.
Tetrahedron, 67(48), 9329-9333 (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)
Sheng-Ming Xie et al.
Analytica chimica acta, 903, 156-163 (2015-12-29)
Molecular organic cages as shape-persistent organic molecules with permanent and accessible cavities have attracted a lot of interest because of their importance as host-guest systems. Herein, we report a chiral porous organic cage (POC) CC9 diluted with a polysiloxane OV-1701
Harold Cruz et al.
Chirality (2018-06-07)
Herein, we report the synthesis of C2 -symmetric sulfonamides as homogeneous and heterogeneous organocatalysts and their application in the enantioselective conjugate 1,4-Michael addition of carbonylic nucleophiles to β-nitrostyrene. Organocatalysts hydrogen bond to β-nitrostyrene and enamine in the transition state, mimicking

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