Trans-1,2-Diaminocyclohexane
From Wikipedia, the free encyclopedia
| Trans-1,2-Diaminocyclohexane | |
|---|---|
 |
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| IUPAC name | (±)-trans-1,2-Cyclohexanediamine |
| Other names | chxn, 1,2-diaminocyclohexane |
| Identifiers | |
| CAS number | [1121-22-8] |
| PubChem | |
| 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 |
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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
- ^ 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.
