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1,4,7-Trithiacyclononane

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1,4,7-Trithiacyclononane
1,4,7-Trithiacyclononane molecule
Names
Preferred IUPAC name 1,4,7-Trithionane
Other names 1,4,7-Trithiacyclononane, Triethylene trisulfide, 9-ane-S3, aneS3
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.150.510 Edit this at Wikidata
EC Number
  • 621-680-0
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H12S3/c1-2-8-5-6-9-4-3-7-1/h1-6H2Key: PQNPKQVPJAHPSB-UHFFFAOYSA-N
  • InChI=1/C6H12S3/c1-2-8-5-6-9-4-3-7-1/h1-6H2Key: PQNPKQVPJAHPSB-UHFFFAOYAS
SMILES
  • C1CSCCSCCS1
  • S1CCSCCSCC1
Properties
Chemical formula C6H12S3
Molar mass 180.35 g/mol
Appearance Colourless solid
Melting point 78 to 81 °C (172 to 178 °F; 351 to 354 K)
Boiling point decomposes
Solubility in water Insoluble
Solubility Chlorocarbons, acetone
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Toxic
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds Thiirane, 1,3,5-Trithiane, 1,4,7-Triazacyclononane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

1,4,7-Trithiacyclononane, also called 9-ane-S3, is the thia-crown ether with the formula (CH2CH2S)3. This cyclic thioether is most often encountered as a tridentate ligand in coordination chemistry, where it forms transition metal thioether complexes.

9-ane-S3 forms complexes with many metal ions, including those considered hard, such as copper(II) and iron(II). Most of its complexes have the formula and are octahedral. The point group of is S6.

Synthesis

This compound was first reported in 1977, and the current synthesis entails the assembly within the coordination sphere of a metal ion followed by decomplexation:

References

  1. Kueppers, H. J.; Wieghardt, K.; Nuber, B.; Weiss, J. W.; Bill, E.; 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 aneS3)(aneS3(O))](ClO4)2·2NaClO4·H2O". Inorganic Chemistry. 26 (22): 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 (15): 2644–2645. doi:10.1021/jo00435a030.
  3. Sellmann, D.; Zapf, L. (1984). "Simple Route to 1,4,7-Trithiacyclononane". Angewandte Chemie. 96 (10): 799–800(2). doi:10.1002/ange.19840961019.
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