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1,4,7-Trithiacyclononane
IUPAC name	1,4,7-Trithionane
Other names	1,4,7-Trithiacyclononane, Triethylene trisulfide, 9-ane-S3, [9]aneS3
Identifiers
CAS number	6573-11-1
PubChem	373835
ChEBI	37418
SMILES	C1CSCCSCCS1
Properties
Molecular formula	C6H12S3
Molar mass	180.35 g/mol
Appearance	Colourless solid
Melting point	78 - 81 °C
Boiling point	Decomp.
Solubility in water	Insoluble
Solubility	Chlorocarbons, acetone
Hazards
R-phrases	R36/37/38
S-phrases	S26, S36
Related compounds
Related compounds	Thiirane, 1,3,5-Trithiane, Triazacylononane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,4,7-Trithiacyclononane, also called 9-ane-S3, is the heterocyclic compound with the formula (CH₂CH₂S)₃. This cyclic thioether is most often encountered as a tridentate ligand in coordination chemistry.

9-ane-S3 forms complexes with many metal ions, including those considered hard, such as copper(II) and iron(II).^[1] Most of its complexes have the formula [M(9-ane-S3)₂]²⁺ and are octahedral.

It was first reported in 1977,^[2] and the current synthesis entails the assembly within the coordination sphere of a metal ion followed by decomplexation.^[3]

[edit] References

1. ^ Kueppers, H. J.; Wieghardt, K.; Nuber, B.; Weiss, J. W.; Bill, E. and Trautwein, A. X. (1987). "Crown Thioether Chemistry of Iron(II/III). Synthesis and Characterization of Low-spin Bis(1,4,7-trithiacyclononane)iron(III) and crystal structure of [FeII([9]aneS3)([9]aneS3(O))](ClO4)2.2NaClO4^.H2O". Inorganic Chemistry 26: 3762–3769(8). doi:10.1021/ic00269a028. 
2. ^ Gerber, D.; Chongsawangvirod, P.; Leung, A. K.; Ochrymowycz, L. A. (1977). "Synthesis of the Torsionally Strained Monocyclic Polythiaether 1,4,7-Trithiacyclononane". Journal of Organic Chemistry 42: 2644–2645(2). 
3. ^ Sellmann, D.; Zapf, L. (1984). "Simple Route to 1,4,7-Trithiacyclononane". Angewandte Chemie 96: 799–800(2). doi:10.1002/ange.19840961019.