1,4,7-Trithiacyclononane

1,4,7-Trithiacyclononane
Names
	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 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:37418 ;
ChemSpider	331656 ;
ECHA InfoCard	100.150.510
PubChem CID	373835;
CompTox Dashboard (EPA)	DTXSID40215934 ;
	InChI InChI=1S/C6H12S3/c1-2-8-5-6-9-4-3-7-1/h1-6H2 Key: PQNPKQVPJAHPSB-UHFFFAOYSA-N ; InChI=1/C6H12S3/c1-2-8-5-6-9-4-3-7-1/h1-6H2 Key: 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
Main hazards	Toxic (T)
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26, S36
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 [77 °F], 100 kPa).
	verify (what is ?)
	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. The point group of [M(9-ane-S3)₂]²⁺ is S₆.

Synthesis

This compound 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]

gollark: So... that 1 returned there... is *that* a tuple?

gollark: Yes, which is pointless.

gollark: Making b be a 1-tuple adds nothing.

gollark: ```haskella = () -- empty/0-tupleb = (()) -- is not 1-tuple, just () - 1-tuple doesn't really add anythingc = ((), ()) -- 2-tuple of 0-tuples```

gollark: 1-tuples are pointless though.

References

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 [FeII([9]aneS3)([9]aneS3(O))](ClO4)2.2NaClO4^.H2O". Inorganic Chemistry. 26 (22): 3762–3769(8). doi:10.1021/ic00269a028.
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.
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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[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 [FeII([9]aneS3)([9]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.