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TCI

CAS 35132-20-8

(1R,2R)-(+)-1,2-Diphenylethylenediamine TCI D2176

(1R,2R)-(+)-1,2-Diphenylethylenediamine TCI D2176
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Description

TCI's (1R,2R)-(+)-1,2-Diphenylethylenediamine is the enantiomeric counterpart of the vicinal chiral diamines widely used in asymmetric synthesis. The compound carries two adjacent stereogenic centres, each bearing a phenyl group and an amino group, which together form a rigid chiral framework whose direction of induction is opposite to that of the (1S,2S) form. Its role in the laboratory is to supply a defined source of chirality for the preparation of ligands, catalysts, and stereochemical auxiliaries, allowing researchers to steer the formation of the desired product enantiomer during the synthesis of active compounds and functional molecules.

The property that makes this material a preferred choice is its capacity for bidentate coordination through both nitrogen atoms, combined with the directed steric hindrance contributed by the two phenyl groups. The space surrounding the reaction centre therefore becomes strongly differentiated, which supports the achievement of high enantiomeric selectivity. The primary amino groups are readily converted into imines, amides, sulfonamides, or thioureas, so a single starting material can give rise to a broad family of catalysts. Its solid form makes accurate weighing straightforward at small scale, while the clearly defined (1R,2R) configuration allows deliberate design of the intended stereochemical outcome.

In Indonesian laboratories, this chiral building block is typically used in university and institutional research groups working on asymmetric methodology, in organic synthesis groups preparing enantioenriched intermediates, and in laboratories developing ligands and organocatalysts. Because it is normally consumed on a small scale within reaction development and screening work, it is generally handled in modest quantities, weighed out precisely for each experiment, and kept together with other moisture-sensitive chiral reagents in the laboratory chemical store.

Laboratory Applications

  • Chiral ligand synthesis — the two nitrogen donors allow straightforward assembly of bidentate ligands whose rigid framework transmits stereochemical information to the metal centre.
  • Organocatalyst preparation — the primary amino groups are easily converted into thiourea, sulfonamide, or amide catalysts used to control enantioselectivity in metal-free transformations.
  • Asymmetric induction studies — the defined (1R,2R) configuration provides a reference sense of induction opposite to the (1S,2S) form, enabling systematic comparison of stereochemical outcomes.
  • Synthesis of enantioenriched intermediates — researchers use it to direct formation of the desired enantiomer when building active compounds and other functional target molecules.
  • Chiral auxiliary and derivative chemistry — condensation to imines and related derivatives gives a versatile platform for generating structurally diverse stereochemical auxiliaries from one starting material.

Specifications

  • Brand: TCI
  • CAS number: 35132-20-8
  • Category: Chemistry > Asymmetric Synthesis > Chiral Building Blocks
  • Chemical name: (1R,2R)-(+)-1,2-Diphenylethylenediamine
  • Physical form: solid, suitable for accurate small-scale weighing
  • Pack sizes: available in research-scale packaging; please confirm the currently offered size when ordering
  • Storage: keep in a closed original container in a cool, dry chemical store

Handling and Storage

Store the material in its original tightly closed container in a cool, dry, and well-ventilated chemical store, away from heat, moisture, and incompatible substances such as strong acids and oxidising agents. Amber glass or the supplier's original packaging is suitable, and containers should be reclosed promptly after each use to limit exposure to atmospheric moisture and carbon dioxide. Weigh and transfer the solid inside a fume hood, using clean, dry spatulas and glassware to avoid cross-contamination between chiral samples. Wear safety glasses, gloves, and a laboratory coat, avoid raising dust, and wash hands after handling. Label all derived solutions with the compound name, configuration, and preparation date, and collect residues and waste according to the laboratory's chemical waste procedures.

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