(1S,2S)-(-)-1,2-diphenylethylenediamine, CAS No. 29841-69-8

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29841-69-8

Catalog No. EBD2204102

CAS 29841-69-8

Name (1S,2S)-(-)-1,2-diphenylethylenediamine

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Basic Information

Synonyms: 2,2'-(E)-ethene-1,2-diyldianiline (1S,2S)-1,2-diphenylethane-1,2-diaminium (1S,2S)-(?)-1,2-Diphenylethylenediamine (1s,2s)-(-)-1,2-diphenylethyle (-)-1,2-diphenylethylenediamine (1s,2s)-1,2-diphenylethylenediamine (1s,2s)-(+)-2-diphenylethylenediamine (1S,2S)-Diphenylethane-1,2-diamine (1S,2S)-(-)-1,2-diphenylethylenediamine (1S,2S)-1,2-Diphenyl-1,2-ethanediamine (1S,2S)-(-)1,2-Diphenylethylenediamine 1,2-ETHANEDIAMINE,1,2-DIPHENYL-,(1S,2S)- (1S,2S)-(+)-1,2-DIPHENYL1,2-ETHANEDIAMINE (1S,2S)-(-)-1,2-DIAMINO-1,2-DIPHENYLETHANE (1S,2S)-(+)-1,2-DIAMINO-1,2-DIPHENYLETHANE (1S,2S)-(-)-1,2-DIPHENYL-1,2-ETHYLENEDIAMINE (1S,2S)-1,2-DIPHENYL-ETHANE-1,2-DIAMINE (1S,2S)-(-)-1,2-Diphenylenediamine (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine

Molecular Formula: C14H16N2

Molecular Weight: 212.29

MDL Number: MFCD00082751

Categories: Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

(1S,2S)-1,2-Diphenylethylenediamine ((1S,2S)-DPEN) is a chiral vicinal diamine compound. It is a white to off-white crystalline solid with the molecular formula C14H16N2. This compound is a key member of the C2-symmetric chiral diamine family, known for its rigid backbone and well-defined spatial arrangement of its phenyl groups and amine functionalities. Its primary and most significant application is as a privileged chiral ligand in asymmetric synthesis. It is famously employed in the Noyori asymmetric hydrogenation catalyst system, where it complexes with ruthenium to form highly efficient catalysts for the enantioselective reduction of ketones and imines. This reaction is fundamental for producing chiral alcohols and amines, which are crucial building blocks in the pharmaceutical and fine chemical industries. The (1S,2S)-enantiomer is essential for producing specific enantiomers of target molecules. Beyond its role as a ligand, (1S,2S)-DPEN also serves as a versatile chiral building block and a chiral resolving agent. Due to its strong chelating ability and defined chirality, it is a valuable precursor for constructing more complex chiral catalysts and auxiliaries used in various enantioselective transformations.

Physical Properties

Melting Point: 83-85 °C(lit.)

Boiling Point: 353.9 °C at 760 mmHg

Flash Point: 199.9 °C

Density: 1.106 g/cm3

Refractivity: -103 ° (C=1, EtOH)

Storage: 2-8°C

Analytical Data

Appearance: white to light yellow crystal powder