''trans''-1,2-Diaminocyclohexane is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...

C₆H₁₀(NH₂)₂. This

diamine A diamine is an amine with exactly two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term ''diamine'' refers mostly to primary diamines, as those are the most reactive. In terms of quantities p ...

is a building block for ''C''₂-symmetric ligands that are useful in

asymmetric catalysis Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecul ...

. A mixture of all three

stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...

s of 1,2-diaminocyclohexane is produced by the

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or S ...

of ''o''-phenylenediamine. It is also side product in hydrogenation of

adiponitrile Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.M. T. Musser, "Adipi ...

. 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 Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally i ...

as the resolving agent. Oxaliplatin-2D-skeletal

Derived ligands

Representative ligands prepared from (1''R'',2''R'')- or (1''S'',2''S'')-1,2-diaminocyclohexane are diaminocyclohexanetetraacetic acid (CyDTAH₄),

Trost ligand The Trost ligand is a diphosphine used in the palladium- catalyzed Trost asymmetric allylic alkylation. Other C2-symmetric ligands derived from ''trans''-1,2-diaminocyclohexane (DACH) have been developed, such as the (''R'',''R'')-DACH- naphthy ...

, and the salen analogue used in the

Jacobsen epoxidation The Jacobsen epoxidation, sometimes also referred to as Jacobsen-Katsuki epoxidation is a chemical reaction which allows enantioselective epoxidation of unfunctionalized alkyl- and aryl- substituted alkenes. It is complementary to the Sharpless e ...

References

{{DEFAULTSORT:Diaminocyclohexane, trans-1,2- Diamines Chelating agents