Trans-1,2-Diaminocyclohexane

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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]

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]

[edit] 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.

[edit] 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.; Coll. Vol. 10: 96.