Trans-1,2-Diaminocyclohexane

Trans-1,2-Diaminocyclohexane

IUPAC name	(±)-trans-1,2-Cyclohexanediamine
Other names	chxn, 1,2-diaminocyclohexane
Identifiers
CAS number	1121-22-8
PubChem	24856187
Properties
Molecular formula	C₆H₁₄N₂
Molar mass	114.19
Appearance	colourless liquid
Melting point	14-15 °C, 272 K, 19 °F
Boiling point	79-81 (15 mm Hg)
Solubility in water	water, organic solvents
Hazards
Flash point	156 °F
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

trans-1,2-Diaminocyclohexane is an organic compound with the formula C₆H₁₀(NH₂)₂. This diamine is a building block for chiral ligands that are useful in asymmetric catalysis.^[1]

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A mixture of cis- and trans-1,2-diaminocyclohexane is produced by the hydrogenation of o-phenylenediamine. The trans isomer can be separated into the two enantiomers using tartaric acid as the resolving agent.^[2]

Ligands derived from chxn

Representative ligands prepared from this diamine are diaminocyclohexanetetraacetic acid (CyDTAH₄), Trost ligand, and the salen analogue used in the Jacobsen epoxidation.

References

^ Cyrille Kouklovsky, Yves Langlois "(1S,2S)-1,2-Diaminocyclohexane1" in Encyclopedia of Reagents for Organic Synthesis, 2003; John Wiley & Sons. DOI: 10.1002/047084289X.rn00145
^ Jay F. Larrow and Eric N. Jacobsen (2004). "(R,R)-N,N'-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst". Org. Synth.; Coll. Vol. 10: 96.

Categories: Polyamines | Chelating agents