# Trithioacetone

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{{Chembox
| ImageFile      = 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane flat.png
| ImageCaption   = 
| PIN            = Hexamethyl-1,3,5-trithiane
| OtherNames     = Trithioacetone<ref name=nih2020/>
| Section1       = {{Chembox Identifiers
| PubChem = 13233
| CASNo = 828-26-2
| ChemSpiderID = 12678
| EC_number = 212-582-5
| UNII = L0ME5B2ZWY
| DTXSID = DTXSID2047723
| ChEMBL = 3187896
| StdInChI = 1S/C9H18S3/c1-7(2)10-8(3,4)12-9(5,6)11-7/h1-6H3
| StdInChIKey = NBNWHQAWKFYFKI-UHFFFAOYSA-N
| SMILES = C1(SC(SC(S1)(C)C)(C)C)(C)C
| Beilstein = 5-19-09-00119
}}
| Section2       = {{Chembox Properties
| C=9|H=18|S=3
| Appearance = 
| Odor = Unpleasant, sulfurous
| Density = 1.0660 to 1.0700 g/mL<ref name=tcicat/>
| Solubility = 
| SolubleOther = 
| MeltingPt = 21.8°C<ref name=pubchem/>
| BoilingPt = 107°C/10mmHg<ref name=tcicat/>
| Viscosity = 
| RefractIndex = 1.5390 to 1.5430<ref name=tcicat/>
| VaporPressure = 
| MagSus = 
}}
| Section4       = {{Chembox Thermochemistry
| DeltaHf = 
| DeltaHc = 
| Entropy = 
}}
| Section7       = {{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
 }}
}}

'''Trithioacetone''' ('''2,2,4,4,6,6-hexamethyl-1,3,5-trithiane''') is an [organic chemical](/source/organic_chemical) with [formula](/source/chemical_formula) {{chem|C|9|H|18|S|3}}. Its [covalent](/source/Covalent_bond) structure is {{chem|[–C(CH|3|)|2|–S–]|3}}, that is, a six-membered ring of alternating [carbon](/source/carbon) and [sulfur](/source/sulfur) atoms, with two [methyl group](/source/methyl_group)s attached to each carbon.<ref name=bres2009/><ref name=tcicat/>  It can be viewed as a derivative of [1,3,5-trithiane](/source/1%2C3%2C5-trithiane), with methyl-group [substituent](/source/substituent)s for all of the hydrogen atoms in that parent structure.

The compound Trithioacetone is a stable [cyclic](/source/cyclic_compound) trimer of [thioacetone](/source/thioacetone) (propane-2-thione), which by itself is an unstable compound.<ref name=lips1970/><ref name=shar1979/> In contrast, the analogous [trioxane](/source/1%2C3%2C5-trioxane) compound, [2,2,4,4,6,6-hexamethyl-1,3,5-trioxane](/source/2%2C2%2C4%2C4%2C6%2C6-hexamethyl-1%2C3%2C5-trioxane) ([Triacetone](/source/Triacetone)), with [oxygen](/source/oxygen) atoms in place of the sulfur atoms, seems to be unstable, while its corresponding monomer [acetone](/source/acetone) (2-propanone) is stable.

==Synthesis==
Trithioacetone was first made in 1889 by Baumann and Fromm, by reaction of [hydrogen sulfide](/source/hydrogen_sulfide) with acetone.<ref name=shar1979/> In the presence of an acidified {{chem|ZnCl|2}} catalyst at 25&nbsp;°C, one obtains a product that is 60–70% trithioacetone, 30–40% of 2,2-propanedithiol, and small amounts of two isomeric impurities, [3,3,5,5,6,6-hexamethyl-1,2,4-trithiane](/source/3%2C3%2C5%2C5%2C6%2C6-hexamethyl-1%2C2%2C4-trithiane) and [4-mercapto-2,2,4,6,6-pentamethyl-1,3-dithiane](/source/4-mercapto-2%2C2%2C4%2C6%2C6-pentamethyl-1%2C3-dithiane).<ref name=shar1979/> The product can also be obtained by [pyrolysis](/source/pyrolysis) of [allyl isopropyl sulfide](/source/allyl_isopropyl_sulfide).<ref name=bail1965/><ref name=bohme1942/>

==Reactions==
Pyrolysis of trithioacetone at 500–650&nbsp;°C and 5–20 [mm of Hg](/source/mm_of_Hg) gives thioacetone, that can be collected by a cold trap at −78&nbsp;°C.
300px|center|Pyrolysis/polymerization between trithioacetone (left) and thioacetone (right).

==Uses==
Trithioacetone is found in some [flavoring agent](/source/flavoring_agent)s.  Its [FEMA](/source/Flavor_and_Extract_Manufacturers_Association) number is 3475.<ref name=mora1980/><ref name=who/><ref name=ohlo1979/><ref name=euro2012/>

==Toxicity==
The [LD<sub>50</sub>](/source/lethal_dose) (oral) in mice is 2.4 g/kg.<ref name=mora1980/><ref name=pubchem/>

==See also==
* [2,4,6-trimethyl-1,3,5-trithiane](/source/2%2C4%2C6-trimethyl-1%2C3%2C5-trithiane)
* [Hexamethylcyclotrisiloxane](/source/Hexamethylcyclotrisiloxane), an analog with a [silicon](/source/silicon)-oxygen ring instead of a carbon-sulfur one.
* [Hexamethylcyclotrisilazane](/source/Hexamethylcyclotrisilazane), with a silicon-[nitrogen](/source/nitrogen) ring.<ref name=brew1948/>
* [2,2,4,4,6,6-hexamethyl-1,3,5-triselena-2,4,6-tristannacyclohexane](/source/2%2C2%2C4%2C4%2C6%2C6-hexamethyl-1%2C3%2C5-triselena-2%2C4%2C6-tristannacyclohexane), with a [tin](/source/tin)-[selenium](/source/selenium) ring.<ref name=mikh2008/><ref name=draeg1978/>

==References==
<references>
<ref name=brew1948>Stuart D. Brewer and Charles P. Haber (1948): "Alkylsilazanes and Some Related Compounds". ''Journal of the American Chemical Society'', volume 70, issue 11, pages 3888–3891. {{doi|10.1021/ja01191a106}}</ref>

<ref name=mikh2008>B. M. Mikhova (2008), "NMR Data for Carbon-13 – C6H18Se3Sn3" in ''Landolt-Börnstein – Group III Condensed Matter'', volume 35 ''Nuclear Magnetic Resonance Data'', subvolume D5, ''Organometallic Compounds''. {{doi|10.1007/978-3-540-74189-3_1362}}</ref>

<ref name=draeg1978>Martin Dräger, Axel Blecher, Hans-Jürgen Jacobsen, Bernt Krebs (1978): "Molekül- und kristallstruktur von hexamethylcyclo-tristannaselenan {{chem|[(CH|3|)|2|SnSe]|3}}". ''Journal of Organometallic Chemistry'', volume 161, issue 3, pages 319–325.  {{doi|10.1016/S0022-328X(00)92243-5}}</ref>

<ref name=euro2012>EUR-Lex (2012): "[https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:32012R0872 Table entry 15.009: Trithioacetone]".   In  ''EU Regulation No. 872/2012'', Document 32012R0872, ''Official Journal of the EU – Series L'', volume 267, pages 1–161.</ref>

<ref name=bohme1942>Horst Bohme, Hans Pfeifer, and Erich Schneider (1942): "Dimeric thioketones". ''Berichte der Deutschen Chemischen Gesellschaft'', volume 75B, issue 7, pages 900–909. {{doi|10.1002/cber.19420750722}} Note: This early report mistakes the trimer for the monomer.</ref>

<ref name=tcicat>TCI America (2020): "[https://www.tcichemicals.com/eshop/en/us/commodity/H1278/ Product H1278: 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane]". Online catalog page, accessed on 2020-01-01.</ref>

<ref name=lips1970>R. D. Lipscomb and W. H. Sharkey (1970): "Characterization and polymerization of thioacetone". ''Journal of Polymer Science – Part A: Polymer Chemistry'', volume 8, issue 8, pages 2187–2196. {{doi|10.1002/pol.1970.150080826}}</ref>

<ref name=bail1965>William J. Bailey and Hilda Chu (1965): "Synthesis of polythioacetone". ''ACS Polymer Preprints'', volume 6, pages=145–155</ref>

<ref name=shar1979>William H. Sharkey (1979): "Polymerization through the carbon-sulfur double bond". ''Polymerization'', series ''Advances in Polymer Science'', volume 17, pages 73–103. {{doi|10.1007/3-540-07111-3_2}}</ref>

<ref name=ohlo1979>G. Ohloff and I. Flament (1979): "The Role of Heteroatomic Substances in the Aroma Compounds of Foodstuffs". In ''Fortschritte der Chemie Organischer Naturstoffe'' (''Progress in the Chemistry of Organic Natural Products''), volume 36, pages 231–283. {{doi|10.1007/978-3-7091-3265-4_2}}</ref>

<ref name=who>World Health Organization (1999): "[https://who.int/food-additives-contaminants-jecfa-database/chemical.aspx?chemID=2916 Trithioacetone]{{dead link|date=December 2021|bot=medic}}{{cbignore|bot=medic}}". Online data sheet in the ''Evaluation of the Joint FAO/WHO Expert Committee on Food Additives (JECFA)''. Accessedd on 2020-01-02.</ref>

<ref name=bres2009>[David S. Breslow](/source/David_S._Breslow), [Herman Skolnik](/source/Herman_Skolnik) (2009): ''Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles'', Part 2; page 712.  Volume 68 of ''Chemistry of Heterocyclic Compounds''. {{isbn|9780470188330}}</ref>

<ref name=nih2020>"[https://pubchem.ncbi.nlm.nih.gov/#tab/sidsrcname=ChemIDplus&query=828-26-2&input_type=text Trithioacetone]". Online chemical data sheet, accessed on 2020-01-01.</ref>

<ref name=pubchem>NCBI PubChem (2010): "[https://pubchem.ncbi.nlm.nih.gov/compound/13233 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane]". Online chemical data sheet, accessed on 2020-01-01.</ref>

<ref name=mora1980>E. J. Moran, O. D. Easterday, and B. L. Oser (1980): "Acute oral toxicity of selected flavor chemicals". ''Drug and Chemical Toxicology'', volume 3, issue 3, pages 249–258.{{PMID|7449655}} {{doi|10.3109/01480548009002221}}</ref>
</references>

Category:Sulfur heterocycles

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Adapted from the Wikipedia article [Trithioacetone](https://en.wikipedia.org/wiki/Trithioacetone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Trithioacetone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.