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
CAS Number	26150-46-9;
3D model (JSmol)	Interactive image;
ChemSpider	19549297;
PubChem CID	427712;
	InChI 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;
	SMILES C1[C@@H](C[C@@H](C[C@@H]1N)N)N;
Properties
Chemical formula	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). Infobox references

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]

Related ligands

Tris(aminomethyl)ethane, another tripodal triamine (CH₃C(CH₂NH₂]₃)

References

^ 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.
^ 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.

[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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