Trans-1,2-Diaminocyclohexane: Difference between revisions
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{{DISPLAYTITLE:''trans''-1,2-Diaminocyclohexane}} |
{{DISPLAYTITLE:''trans''-1,2-Diaminocyclohexane}} |
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{{chembox |
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|Name=''trans''-1,2-Diaminocyclohexane |
|Name=''trans''-1,2-Diaminocyclohexane |
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|ImageFile=Trans-1,2-Diaminocyclohexane Structural Formulae V.1.svg |
|ImageFile=Trans-1,2-Diaminocyclohexane Structural Formulae V.1.svg |
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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_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SSJXIUAHEKJCMH-WDSKDSINSA-N |
| StdInChIKey = SSJXIUAHEKJCMH-WDSKDSINSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=1121-22-8 |
| CASNo=1121-22-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 37EKL250EE |
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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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| BoilingPtC = 79 to 81 |
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| MeltingPtCH = 15 |
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| BoilingPt_notes = 15 mmHg |
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| BoilingPtCL = 79 |
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| BoilingPtCH = 81 |
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| Boiling_notes = 15 mm Hg |
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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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| Autoignition= |
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'''''trans''-1,2-Diaminocyclohexane''' is an [[organic compound]] with the [[chemical formula|formula]] C<sub>6</sub>H<sub>10</sub>(NH<sub>2</sub>)<sub>2</sub>. |
'''''trans''-1,2-Diaminocyclohexane''' is an [[organic compound]] with the [[chemical formula|formula]] C<sub>6</sub>H<sub>10</sub>(NH<sub>2</sub>)<sub>2</sub>. This [[diamine]] is a building block for [[C2-Symmetric ligands|''C''<sub>2</sub>-symmetric ligand]]s that are useful in [[asymmetric catalysis]].<ref>{{cite book|doi=10.1002/047084289X.rn00145|chapter=(1S,2S)-1,2-Diaminocyclohexane|title=Encyclopedia of Reagents for Organic Synthesis|year=2003|last1=Kouklovsky|first1=Cyrille|last2=Langlois|first2=Yves|isbn=0471936235}}</ref> |
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A mixture of |
A mixture of all three [[stereoisomer]]s of [[1,2-diaminocyclohexane]] is produced by the [[hydrogenation]] of [[O-Phenylenediamine|''o''-phenylenediamine]]. It is also side product in hydrogenation of [[adiponitrile]]. The racemic ''trans'' isomer (1:1 mixture of (1''R'',2''R'')-1,2-diaminocyclohexane and (1''S'',2''S'')-1,2-diaminocyclohexane) can be separated into the two enantiomers using enantiomerically pure [[tartaric acid]] as the resolving agent.<ref>{{OrgSynth | author = Jay F. Larrow and Eric N. Jacobsen | title = (''R'',''R'')-''N'',''N''{{'}}-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst | collvol = 10 | collvolpages = 96| year = 2004 | prep = V75P0001}}</ref> |
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[[File:Oxaliplatin-2D-skeletal.svg|thumb|left|204px|[[Oxaliplatin]], a complex of R,R-diaminocyclohexane, is an important anticancer drug.]] |
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==Derived ligands== |
==Derived ligands== |
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{{reflist}} |
{{reflist}} |
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{{DEFAULTSORT |
{{DEFAULTSORT:Diaminocyclohexane, trans-1, 2-}} |
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[[Category: |
[[Category:Diamines]] |
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[[Category:Chelating agents]] |
[[Category:Chelating agents]] |
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[[Category:Cyclohexanes]] |
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[[de:1,2-Diaminocyclohexan]] |
Latest revision as of 22:24, 5 August 2024
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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UNII | |
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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 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).
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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 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]
Derived ligands
[edit]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
[edit]- ^ 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.