trans-1,2-Diaminocyclohexane
From Self-sufficiency
| trans-1,2-Diaminocyclohexane | |
|---|---|
| File:Trans-1,2-Diaminocyclohexane Structural Formulae V.1.svg | |
| (±)-trans-1,2-Cyclohexanediamine | |
| Other names chxn, 1,2-diaminocyclohexane | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 1121-22-8 |
| PubChem | 24856187 |
| style="background: #F8EABA; text-align: center;" colspan="2" | 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 |
| style="background: #F8EABA; text-align: center;" colspan="2" | Hazards | |
| Flash point | 156 °F |
| 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]
Ligands derived from chxn
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
- ↑ 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 Missing or empty
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