1,4,7-Trithiacyclononane

Chembox new
ImageFile = 9-ane-S3.svg
ImageSize =
IUPACName = 1,4,7-Trithionane
OtherNames = 1,4,7-Trithiacyclononane, Triethylene trisulfide, 9-ane-S3, [9] aneS₃
Section1 = Chembox Identifiers
CASNo = 6573-11-1
PubChem = 373835
SMILES = C1CSCCSCCS1
ChEBI = 37418
Section2 = Chembox Properties
Formula = C₆H₁₂S₃
MolarMass = 180.35 g/mol
Appearance = Colourless solid
Density =
MeltingPt = 78 - 81 °C
BoilingPt = Decomp.
Solubility = Insoluble
SolubleOther = Chlorocarbons, acetone
Section7 = Chembox Hazards
MainHazards = Toxic (T)
RPhrases = R36/37/38
SPhrases = S26, S36
FlashPt =
Autoignition =
Section8 = Chembox Related
OtherAnions =
OtherCations =
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Function =
OtherCpds = Thiirane, 1,3,5-Trithiane, Triazacylononane

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). [cite journal | author = Kueppers, H. J.; Wieghardt, K.; Nuber, B.; Weiss, J. W.; Bill, E. and Trautwein, A. X. | date = 1987 | title = 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 | journal = Inorganic Chemistry | volume = 26 | issue = | pages = 3762–3769(8) | pmid = | doi = | url = | accessdate = ] Most of its complexes have the formula [M(9-ane-S3)₂] ²⁺ and are octahedral.

It was first reported in 1977, [cite journal | author = Gerber, D.; Chongsawangvirod, P.; Leung, A. K.; Ochrymowycz, L. A. | date = 1977 | title = Synthesis of the Torsionally Strained Monocyclic Polythiaether 1,4,7-Trithiacyclononane | journal = Journal of Organic Chemistry | volume = 42 | issue = | pages = 2644–2645(2) | pmid = | doi = | url = | accessdate = ] and the current synthesis entails the assembly within the coordination sphere of a metal ion followed by decomplexation. [cite journal | author = Sellmann, D.; Zapf, L. | date = 1984 | title = Simple Route to 1,4,7-Trithiacyclononane | journal = Angewandte Chemie | volume = 96 | issue = | pages = 799–800(2) | pmid = | doi = | url = | accessdate = ]

References