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

• ChemBase ID: 68709
• Molecular Formular: C14H16N2
• Molecular Mass: 212.29024
• Monoisotopic Mass: 212.13134852
• SMILES: [C@H]([C@@H](N)c1ccccc1)(N)c1ccccc1
• Canonical SMILES: N[C@H]([C@H](c1ccccc1)N)c1ccccc1
• InChI: 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
• InChIKey: PONXTPCRRASWKW-KBPBESRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S)-1,2-diphenylethane-1,2-diamine
• IUPAC Traditional name: diphenylethylenediamine
• Synonyms: (1S,2S)-(-)-1,2-Diphenylethylenediamine; DPEN; Diphenylethylenediamine; (1S,2S)-(-)-1,2-Diphenylethylenediamine; (1S,2S)-(-)-1,2-Diphenylethylenediamine; (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine; (1S,2S)-(-)-1,2-Diamino-1,2-diphenylethane; (1S,2S)-(-)-1,2-Diphenylethane-1,2-diamine; (1S,2S)-(-)-1,2-二氨基-1,2-二苯基乙烷; (1S,2S)-(-)-1,2-二苯基乙二胺; (1S,2S)-(+)-1,2-二苯基-1,2-乙二胺

Database IDs

• CAS Number: 29841-69-8; 35132-20-8
• MDL Number: MFCD00082751
• Beilstein Number: 3201645
• PubChem SID: 24866757; 162034439; 24862409
• PubChem CID: 6931238
• CHEMBL: 467308
• Chemspider ID: 5305408
• Wikipedia Title: Diphenylethylenediamine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.8482778
• LogD (pH = 7.4): 0.31417987
• Log P: 2.1460378
• Molar Refractivity: 66.4342 cm^3
• Polarizability: 26.751324 Å^3
• Polar Surface Area: 52.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Slightly in water
• Apperance: White crystals
• Melting Point: 79-83 °C; 80-84°C; 80-85°C; 83-85 °C(lit.)
• Optical Rotation: [α]20/D -102°, c = 1 in ethanol; [α]20/D -105±3°, c = 1% in methanol; -102 (c=1 in methanol)

Safety Information

• Storage Warning: Air Sensitive; Harmful/Irritant/Corrosive/Air Sensitive/Store under Argon/Keep Cold; IRRITANT
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: UN3259
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 34; 36/37/38
• Safety Statements: 26-36; 26-36/37/39-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H314-H318; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC); 95+%; 97%
• Grade: purum
• Optical Purity: ee: 98% (GLC)
• Linear Formula: [C6H5CH(NH2)-]2

DETAILS

Sigma Aldrich - 364002

Application
Versatile ligand for the formation of metal complexes.1 Used in the synthesis of chiral tropocoronands which have potential utility in asymmetric catalysis.2
Packaging
500 mg in glass bottle

REFERENCES

• Chiral auxiliary and solvation agent; see preceding entry.
• Co-catalyst in the Ru catalyzed enantioselective hydrogenation of aromatic ketones: J. Am. Chem. Soc., 117, 2675 (1995).
• For synthesis of enantiopure ethylenediamines by chirality transfer (condensation with diketones followed by reductive cleavage), see: J. Org. Chem ., 57, 6653 (1992).