1,4,7-Trithiacyclononane

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1,4,7-Trithiacyclononane
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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
Main hazards Toxic (T)
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 disclaimer and 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]

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). 
  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). 

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