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Description
TCI D3930 meso-1,2-Diphenylethylenediamine is a vicinal diamine that carries a phenyl group on each of two adjacent carbon atoms. Its meso configuration gives the molecule an internal plane of symmetry, so that despite containing stereocentres the compound as a whole is not optically active. As a non-heterocyclic building block, it serves as a basic scaffold for constructing ligands, macrocycles, and a wide range of nitrogen-containing derivatives in the organic synthesis laboratory. The presence of two primary amine groups in neighbouring positions makes it a natural chelating reagent for many transition metals.
The property that leads researchers to select this compound is its ability to form stable five-membered chelate rings together with metal ions, combined with two phenyl groups that impose a distinctive steric environment around the metal centre. The meso configuration also makes it an especially valuable comparison diastereomer against the (R,R) and (S,S) forms: by comparing the behaviour of catalysts or complexes built from these different forms, researchers can separate steric effects from genuine chirality effects. In addition, both primary amine groups are readily converted into imines, amides, sulfonamides, or ureas through standard reactions.
In Indonesian laboratories, this material typically finds a place in university and institutional research groups working on organic synthesis, coordination chemistry, and homogeneous catalysis. It is normally handled at bench scale in fume-hooded synthesis laboratories, where small quantities are weighed out for ligand preparation and condensation reactions. Because it functions primarily as a synthetic intermediate rather than a routine analytical reagent, it is generally ordered in research-scale quantities as specific projects require it.
Laboratory Applications
- Chiral and achiral ligand synthesis: the two adjacent primary amines readily condense with carbonyl compounds to give diimine ligands used across coordination chemistry research programmes.
- Transition metal complex preparation: the vicinal diamine motif binds metal centres through a stable five-membered chelate ring, giving well-defined and reproducible complexes for structural study.
- Catalysis mechanism studies: as the meso diastereomer, it provides a matched steric but non-chiral reference against (R,R) and (S,S) analogues, isolating chirality contributions to catalyst performance.
- Macrocycle and cage construction: the rigid diphenyl backbone acts as a defined corner unit in template-directed macrocyclisation, helping control ring size and cavity geometry.
- Nitrogen derivative preparation: both amine groups convert cleanly into amides, sulfonamides, imines, and ureas, making it a versatile starting point for derivative libraries in synthesis laboratories.
Specifications
- Brand: TCI
- CAS number: 951-87-1
- Catalogue number: D3930
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in research-scale laboratory pack sizes; please confirm the currently offered packaging when ordering
- Storage: store according to the manufacturer's instructions stated on the product label and safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, and well-ventilated area, away from direct sunlight, heat sources, and incompatible chemicals such as strong acids and oxidising agents. Keep the material in its original manufacturer packaging or in a clean, clearly labelled, chemically compatible container, and reseal it promptly after each use to limit exposure to atmospheric moisture and carbon dioxide, to which primary amines are sensitive. Handle all weighing and transfer operations in a fume hood while wearing safety glasses, chemical-resistant gloves, and a laboratory coat. Avoid inhalation of dust and contact with skin or eyes. Always consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated materials through your institution's chemical waste procedures.
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