364010
(1R,2R)-(+)-1,2-Diphenylethylenediamine
97%
Synonym(s):
(1R,2R)- DPEDA, (1R,2R)-DPEN, (1R,2R)-(+)-1,2-Diamino-1,2-diphenylethane
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About This Item
Linear Formula:
[C6H5CH(NH2)-]2
CAS Number:
Molecular Weight:
212.29
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2369988
Assay:
97%
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
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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(1R, 2R)-DPEN-derived triazolium salts for enantioselective oxodiene Diels?Alder reactions.
Rong Z Q, et al.
Tetrahedron, 67(48), 9329-9333 (2011)
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)