What is 1 2 diaminocyclohexane?

1,2-Diaminocyclohexane

1,2-Diaminocyclohexane, also known as 1,2-cyclohexanediamine (DACH), is an organic compound with the formula C6H10(NH2)2. It exists as cis and trans isomers.

Key Properties & Information:

• Isomerism: The compound exists as cis and trans isomers. The trans isomer is chiral, existing as two enantiomers, (1R,2R)- and (1S,2S)-1,2-diaminocyclohexane. The cis isomer is achiral (not chiral). Understanding the differences in these isomers is crucial in applications. More information about isomerism can be found.

• Synthesis: It can be synthesized through various routes, including the hydrogenation of 1,2-diaminobenzene (phenylenediamine). The relative ratios of cis and trans isomers can be controlled through catalyst choice and reaction conditions. More information about synthesis can be found.

• Chirality: The trans-1,2-diaminocyclohexane exists as a pair of enantiomers. These enantiomers are important in asymmetric catalysis and chiral resolution. More information about chirality can be found.

• Applications:

  • Ligand in Coordination Chemistry: 1,2-Diaminocyclohexane is a common bidentate ligand in coordination chemistry, especially in the synthesis of metal complexes used as catalysts. Platinum complexes of DACH are important chemotherapeutic agents.
  • Chiral Resolving Agent: The enantiomerically pure trans isomers can be used as chiral resolving agents to separate racemic mixtures of other chiral compounds.
  • Pharmaceuticals: Platinum-based complexes containing DACH ligands, such as oxaliplatin, are used as anti-cancer drugs. Learn more about pharmaceuticals.
  • Asymmetric Catalysis: DACH derivatives are utilized as chiral ligands in asymmetric catalysis.

• Safety: Diamines can be irritating to the skin, eyes, and respiratory system. Appropriate safety precautions should be taken when handling this compound.