trans-1,2-Diaminocyclohexane

*trans*-1,2-Diaminocyclohexane
Names
	IUPAC name (±)-trans-1,2-Cyclohexanediamine
	Other names 1,2-Diaminocyclohexane; chxn
Identifiers
CAS Number	1121-22-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	420572 ;
ECHA InfoCard	100.127.756
PubChem CID	479307;
UNII	37EKL250EE ;
	InChI InChI=1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m0/s1 Key: SSJXIUAHEKJCMH-WDSKDSINSA-N ; 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;
	SMILES N[C@H]1CCCC[C@@H]1N;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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]

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

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

[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; Collected Volumes, vol. 10, p. 96.

[1]

[2]