trans-1,2-Diaminocyclohexane

trans-1,2-Diaminocyclohexane
IUPAC name (±)-trans-1,2-Cyclohexanediamine
Other names 1,2-Diaminocyclohexane; chxn
Identifiers
CAS number	1121-22-8
PubChem	479307
ChemSpider	420572 Y
Jmol-3D images	Image 1
SMILES N[C@H]1CCCC[C@@H]1N
InChI InChI=1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m0/s1 Y Key: SSJXIUAHEKJCMH-WDSKDSINSA-N Y 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
Properties
Molecular formula	C6H14N2
Molar mass	114.19 g mol−1
Appearance	Colorless liquid
Density	0.951 g/cm3
Melting point	14-15 °C, 287-288 K, 57-59 °F
Boiling point	79-81 °C, 352-354 K, 174-178 °F (15 mm Hg)
Hazards
Flash point	156 °F (69 °C)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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]

A mixture of cis- and trans-1,2-diaminocyclohexane is produced by the hydrogenation of o-phenylenediamine. 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]

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. ^ 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
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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=V75P0001 ; Coll. Vol. 10: 96