CAS 29841-69-8 (1S,2S)-(-)-1,2-Diphenylethylenediamine

Synonyms

1S,2S)-1,2-Diphenylethane-1,2-diamine; (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine

IUPAC Name

(1S,2S)-1,2-diphenylethane-1,2-diamine

Molecular Weight

212.29

Molecular Formula

C14H16N2

Canonical SMILES

C1=CC=C(C=C1)C(C(C2=CC=CC=C2)N)N

InChI

PONXTPCRRASWKW-KBPBESRZSA-N

InChI Key

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-/m0/s1

Boiling Point

353.9 °C at 760 mmHg

Melting Point

83-85 °C-lit.

Purity

98%

Appearance

White to pale yellow crystal

Storage

2-8°C

Complexity

171

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

212.131348519

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Isomeric SMILES

C1=CC=C(C=C1)[C@@H]([C@H](C2=CC=CC=C2)N)N

Monoisotopic Mass

212.131348519

Rotatable Bond Count

Topological Polar Surface Area

52 Å²

Application

(1S,2S)-(-)-1,2-Diphenylethylenediamine is a versatile, chiral compound that appears as a white to light yellow crystal powder. Its primary purpose is to facilitate the synthesis of enantiopure ethylenediamines through chirality transfer, utilizing condensation with diketones followed by reductive cleavage. Additionally, it serves as a co-catalyst in ruthenium-catalyzed enantioselective hydrogenation of aromatic ketones, and acts as a ligand for the formation of metal complexes. This compound is instrumental in the synthesis of chiral tropocoronands, which are valuable in asymmetric catalysis. Furthermore, it functions effectively as a chiral resolving agent, a precursor of chiral auxiliaries, and as a chiral solvating agent in NMR studies, highlighting its extensive utility in various chemical applications.

March 18, 2025

Essential for Enantioselective Hydrogenation

Using (1S,2S)-(-)-1,2-Diphenylethylenediamine from Alfa Chemistry was seamless in my research. Its role as a co-catalyst in Ru-catalyzed hydrogenation and versatile ligand formation enhanced our asymmetric catalysis synthesis significantly.