Cis,cis-1,3,5-Triaminocyclohexane

cis,cis-1,3,5-Triaminocyclohexane
Names
Preferred IUPAC name
(1s,3s,5s)-Cyclohexane-1,3,5-triamine
Other names
TACH; cis,cis-Cyclohexane-1,3,5-triamine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H15N3/c7-4-1-5(8)3-6(9)2-4/h4-6H,1-3,7-9H2/t4-,5+,6-
    Key: UYAUGHKQCCCFDK-FPFOFBBKSA-N
  • C1[C@@H](C[C@@H](C[C@@H]1N)N)N
Properties
C6H15N3
Molar mass 129.207 g·mol−1
Appearance Colorless liquid
Boiling point 285 °C (545 °F; 558 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Not to be confused with triazacyclohexane.

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.

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. ^ 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. ^ 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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