Cis,cis-1,3,5-Triaminocyclohexane

<i>cis</i>,<i>cis</i>-1,3,5-Triaminocyclohexane

cis,cis-1,3,5-Triaminocyclohexane

Chemical compound

cis,cis-1,3,5-Triaminocyclohexane is an organic compound with the formula (CH2CHNH2)3. It is a triamine. Of the many isomers possible for triaminocyclohexane, the cis,cis-1,3,5-derivative has attracted attention because it is a common tripodal ligand, abbreviated as tach. It is a colorless oil. It is a popular tridentate ligand in coordination chemistry.

Quick Facts Names, Identifiers ...
Not to be confused with triazacyclohexane.

It is prepared from the triscarbamate of cyclohexane. The latter is generated via the Curtius rearrangement starting from cyclohexanetricarboxylic acid.[1]

Structure of [Ni(TACH)(H2O)3]2+ (color code: blue = nitrogen, red = oxygen; dark blue = nickel).[2]

References

  1. [1]
    Bowen, Tom; Planalp, Roy P.; Brechbiel, Martin W. (1996). "An improved synthesis of cis,cis-1,3,5-triaminocyclohexane. Synthesis of novel hexadentate ligand derivatives for the preparation of gallium radiopharmaceuticals". Bioorganic & Medicinal Chemistry Letters. 6 (7): 807–810. doi:10.1016/0960-894X(96)00110-2.
  2. [2]
    Schwarzenbach, Gerold; Bürgi, Hans-Beat; Jensen, William P.; Lawrance, Geoffrey A.; Mønsted, Lene; Sargeson, Alan M. (1983). "Acid cleavage of nickel(II) complexes containing cis,cis-1,3,5-cyclohexanetriamine (TACH), crystal structure of [Ni(tach)(H2O)3](NO3)2, and a correlation between the structure and reactivity of nickel–polyamine complexes". Inorganic Chemistry. 22 (26): 4029–4038. doi:10.1021/ic00168a042.
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