Trans-1,2-Diaminocyclohexane: Difference between revisions
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|OtherNames= 1,2-Diaminocyclohexane; chxn |
|OtherNames= 1,2-Diaminocyclohexane; chxn |
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|Section1= {{Chembox Identifiers |
|Section1= {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 420572 |
| ChemSpiderID = 420572 |
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| InChI = 1/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m0/s1 |
| InChI = 1/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m0/s1 |
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| StdInChIKey = SSJXIUAHEKJCMH-WDSKDSINSA-N |
| StdInChIKey = SSJXIUAHEKJCMH-WDSKDSINSA-N |
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| CASNo=1121-22-8 |
| CASNo=1121-22-8 |
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| PubChem = 479307 |
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| SMILES = N[C@H]1CCCC[C@@H]1N |
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|Section2= {{Chembox Properties |
|Section2= {{Chembox Properties |
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| C=6|H=14|N=2 |
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| Appearance=Colorless liquid |
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| Density=0.951 g/cm<sup>3</sup> |
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| MeltingPtC = 14 to 15 |
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| MeltingPtCH = 15 |
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| BoilingPtCH = 81 |
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|Section3= {{Chembox Hazards |
|Section3= {{Chembox Hazards |
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| MainHazards= |
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| FlashPtF = 156 |
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| AutoignitionPtC = |
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Revision as of 20:46, 19 March 2015
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| Names | |
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| IUPAC name
(±)-trans-1,2-Cyclohexanediamine
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| Other names
1,2-Diaminocyclohexane; chxn
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.127.756 |
PubChem CID
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| Properties | |
| 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 mm Hg |
| 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).
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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 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
- ^ 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". Organic Syntheses; Collected Volumes, vol. 10, p. 96.