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Chemical Structure| 35132-20-8 Chemical Structure| 35132-20-8
Chemical Structure| 35132-20-8

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Synonyms: (+)-1,2-Diphenylethylenediamine; (+)-Stilbenediamine

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Product Citations

Product Citations

Jameson ; Bailey Lauren ;

Abstract: Enantioselective additions of malonate esters to nitroalkenes can be catalyzed by a variety of salts of chiral cobalt(III) trications [Co(1,2-diamine)3] 3+ in the presence of nitrogen donor bases in acetone. Catalysts that feature enantiopure 1,2-diphenylethylenediamine are particularly effective, and the base can also be incorporated into one of the counter anions, for example a (substituted) nicotinate. This study shows that such additions can be carried out under solvent free conditions and with reduced reaction times using ball milling, further enhancing the "green" credentials of this large family of earth-abundant-metal catalysts. The effect of various reaction variables are probed (base, counter anions, loading, time, quantity of balls, etc.), and the optimized conditions applied to twelve nitroalkenes, affording products in average yields and ee values of 89% and 74%. The enantioselectivities appear slightly lower than for analogous reactions in solution (0 °C), and possible factors and remedies are discussed. These tricationic Co(III) species were also analyzed using Electrospray Ionization-Mass Spectrometry to determine if the anions “fly” with the cation for further mechanistic analysis. Only half showed anions “flying” with the cation: Λ-(S,S)-23+ 2Cl–, Λ/D-(S,S)-23+ 2Cl–BArf –, Λ-(S,S)-23+ Cl–BArf –Nic–, and Λ-(S,S)-23+ 3BF4 –. While anionic impurities were found in several cases, the larger, bulkier anions seemed to become ionized themselves leaving no indication of intact cation-anion species post-ionization. Enhanced purification techniques are shown to improve the removal of unwanted anions.

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Product Details of (R,R)-DPEN

CAS No. :35132-20-8
Formula : C14H16N2
M.W : 212.29
SMILES Code : N[C@H](C1=CC=CC=C1)[C@@H](C2=CC=CC=C2)N
Synonyms :
(+)-1,2-Diphenylethylenediamine; (+)-Stilbenediamine
MDL No. :MFCD00082769
InChI Key :PONXTPCRRASWKW-ZIAGYGMSSA-N
Pubchem ID :2724998

Safety of (R,R)-DPEN

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of (R,R)-DPEN

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 35132-20-8 ]

[ 35132-20-8 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 421-83-0 ]
  • [ 35132-20-8 ]
  • [ 121788-73-6 ]
  • 2
  • [ 1646-53-3 ]
  • [ 35132-20-8 ]
  • 1,2-diphenyl-<i>N</i>,<i>N</i>'-bis-(2,3,5,6-tetramethyl-phenyl)-ethane-1,2-diamine [ No CAS ]
  • 3
  • [ 35132-20-8 ]
  • [ 21286-54-4 ]
  • C34H44N2O6S2 [ No CAS ]
  • 4
  • [ 35132-20-8 ]
  • [ 475-11-6 ]
  • [ 1105044-55-0 ]
  • 5
  • [ 35132-20-8 ]
  • [ 21286-54-4 ]
  • [ 676270-67-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; for 5h; General procedure: To a stirred solution of triethylamine (1.39 mL, 10 mmol) and (1S,2S)-1,2-diphenylethane-1,2-diamine (1.06 g, 5 mmol) in CH2Cl2 (15 mL) at 0 C, (1S)-(+)-10-camphorsulfonyl chloride 1 (1.25 g, 5 mmol) in CH2Cl2 (5 mL) was added dropwise. Then after stirring at the same temperature for 1 h, and then at room temperature for another 4 h, the reaction mixture was quenched with water and extracted with CH2Cl2. The organic phase was separated and dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by crystallization with ethyl acetate and methanol to afford (S,S,S)-CsDPEN as a white solid (1.04 g, 48% yield).
  • 6
  • [ 34374-88-4 ]
  • [ 35132-20-8 ]
  • C60H48N6O6 [ No CAS ]
 

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