Trans-1,2-Diaminocyclohexane

Chembox new
ImageFile=Chxn.pngImageSize=300px
IUPACName=(±)-trans-1,2-Cyclohexanediamine
OtherNames= chxn, 1,2-diaminocyclohexane
Section1= Chembox Identifiers
CASNo=1121-22-8
PubChem=24856187
SMILES=
Section2= Chembox Properties
Formula=C₆H₁₄N₂
MolarMass=114.19
Appearance=colourless liquid
Density=
MeltingPtC=14-15
BoilingPt=79-81 (15 mm Hg)
Solubility=water, organic solvents
Section3= Chembox Hazards
MainHazards=
FlashPt=156 °F
Autoignition=

"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. [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]

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. [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]

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.

References