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Description
TCI D4740, CAS number 885280-64-8, is N,N-Dimethyl-1,3-cyclohexanediamine supplied as a mixture of cis and trans isomers. The compound is a cyclic aliphatic diamine carrying one primary amine group and one dimethylated tertiary amine group separated by a cyclohexane framework. This difference in substitution level between the two nitrogen atoms makes it an attractive building block in the laboratory, because reactions can be directed selectively at the primary amine while the tertiary amine remains available as an internal base or as a coordination site for metals.
The characteristic that leads researchers to select this material is the cyclohexane framework, which restricts conformational freedom so that the distance and orientation between the two nitrogen atoms become relatively well defined. Properties of this kind matter in ligand design, since chelation geometry contributes to the stability and activity of the metal complexes that are formed. Aliphatic diamines bearing different substitution patterns at each nitrogen have been widely studied as supporting ligands for copper-catalysed coupling reactions and as scaffolds for organocatalysts.
Supply as a mixture of cis and trans isomers also makes preliminary studies more convenient before researchers commit to a single isomer. In Indonesian laboratories the compound is typically used in synthetic and catalysis research groups at universities and research institutes, where a differentiated diamine is needed for exploratory ligand screening, for the preparation of derivatives through the primary amine, or as a starting framework in small-scale method development work.
Laboratory Applications
Ligand synthesis for copper-catalysed coupling: the defined nitrogen spacing on the cyclohexane framework supports chelation, and aliphatic diamines of this type are widely studied as supporting ligands for such reactions.
Selective functionalisation at the primary amine: the difference in substitution level allows acylation, alkylation or condensation to be directed at the primary nitrogen while the dimethylated tertiary amine is left untouched.
Organocatalyst scaffold preparation: the compound provides a conformationally restricted diamine backbone, and diamines with differentiated nitrogen atoms are investigated as frameworks for organic catalysts.
Metal complex preparation and screening: the tertiary amine remains available as a coordination site for metals, so the material serves as a chelating unit whose geometry influences complex stability and activity.
Exploratory synthetic method development: supply as a cis and trans mixture makes the material convenient for preliminary experiments before a researcher decides to work with a single isolated isomer.
Specifications
Brand: TCI
CAS number: 885280-64-8
Chemical name: N,N-Dimethyl-1,3-cyclohexanediamine (cis- and trans- mixture)
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes: available in the standard research pack sizes offered by TCI for this catalogue item
Storage: keep in the tightly closed original container, protected from air and moisture
Handling and Storage
Store the container tightly closed in a cool, dry and well-ventilated area, away from heat sources, ignition sources and incompatible materials such as strong acids and oxidising agents. Aliphatic amines are hygroscopic and readily absorb carbon dioxide from the air, so the original supplier container should be kept sealed and reclosed promptly after each withdrawal; handling under an inert atmosphere is advisable for moisture-sensitive work. Dispense inside a fume hood while wearing safety glasses, chemically resistant gloves and a laboratory coat, since amines of this class are corrosive and have a strong odour. Avoid contact with skin and eyes and avoid breathing the vapour. Always consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated materials through the laboratory's chemical waste route.
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