trans-1,2-Diaminocyclohexane

trans-1,2-Diaminocyclohexane is an organic compound with the formula C6H10(NH2)2. This diamine is a building block for C2-symmetric ligands that are useful in asymmetric catalysis.[1]

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trans-1,2-Diaminocyclohexane
Names
IUPAC name
(±)-trans-1,2-Cyclohexanediamine
Other names
1,2-Diaminocyclohexane; chxn
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.127.756
UNII
  • InChI=1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m0/s1 checkY
    Key: SSJXIUAHEKJCMH-WDSKDSINSA-N checkY
  • InChI=1/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m0/s1
    Key: SSJXIUAHEKJCMH-WDSKDSINBK
  • N[C@H]1CCCC[C@@H]1N
Properties
C6H14N2
Molar mass 114.192 g·mol−1
Appearance Colorless liquid
Density 0.951 g/cm3
Melting point 14 to 15 °C (57 to 59 °F; 287 to 288 K)
Boiling point 79 to 81 °C (174 to 178 °F; 352 to 354 K) 15 mmHg
Hazards
Flash point 69 °C; 156 °F; 342 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

A mixture of all three stereoisomers of 1,2-diaminocyclohexane is produced by the hydrogenation of o-phenylenediamine. It is also side product in hydrogenation of adiponitrile. The racemic trans isomer (1:1 mixture of (1R,2R)-1,2-diaminocyclohexane and (1S,2S)-1,2-diaminocyclohexane) can be separated into the two enantiomers using enantiomerically pure tartaric acid as the resolving agent.[2]

Oxaliplatin, a complex of R,R-diaminocyclohexane, is an important anticancer drug.

Derived ligands

Representative ligands prepared from (1R,2R)- or (1S,2S)-1,2-diaminocyclohexane are diaminocyclohexanetetraacetic acid (CyDTAH4), Trost ligand, and the salen analogue used in the Jacobsen epoxidation.

References
  1. Kouklovsky, Cyrille; Langlois, Yves (2003). "(1S,2S)-1,2-Diaminocyclohexane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00145. ISBN 0471936235.
  2. 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". Organic Syntheses.; Collective Volume, vol. 10, p. 96
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