1,3,5-Trithiane

1,3,5-Trithiane

Chembox new
ImageFile1 = 1,3,5-Trithiane.png ImageSize1 = 100px
ImageFileL2 = 1,3,5-trithiane-from-xtal-3D-balls.png ImageFileR2 = 1,3,5-trithiane-from-xtal-3D-vdW.png IUPACName = 1,3,5-Trithiane
OtherNames = Thioformaldehyde trimer, Trimethylentrisulfide, Trimethylene trisulfide, Trithioformaldehyde, 1,3,5-Trithiacyclohexane, sym-Trithiane, Thioform, s-Trithiane
Section1 = Chembox Identifiers
CASNo = 291-21-4
EINECS = 206-029-7
PubChem = 9264
ChemSpiderID = 8907
SMILES = C1SCSCS1
Section2 = Chembox Properties
Formula = C3H6S3
MolarMass = 138.27
Appearance = Colourless solid
Density = 1.6374 g/cm3David R. Lide, ed. "Handbook of Chemistry and Physics, 85th Edition", Internet Version 2005. CRC Press, 2005.]
MeltingPt = 215-220 °C
BoilingPt =
Solubility = Slightly soluble
SolubleOther = Benzene
Section3 = Chembox Hazards
MainHazards = Toxic (T)
NFPA-H = 1
NFPA-F = 1
NFPA-R = 0
NFPA-O =
RPhrases =
SPhrases = S22, S24/25
FlashPt =
Autoignition =

1,3,5-Trithiane is the chemical compound with the formula (CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide. [Bost, R. W.; Constable, E. W. "sym-Trithiane" Organic Syntheses, Collected Volume 2, p.610 (1943). http://www.orgsyn.org/orgsyn/pdfs/CV2P0610.pdf]

Trithiane is a building block molecule in organic synthesis, being a masked source of formaldehyde. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which in turn can be alkylated. [Seebach, D.; Beck, A. K. “Aldehydes From "sym"-Ttrithiane: "n"-Pentadecanal” Organic Syntheses, Collected Volume 6, p.869 (1988). http://www.orgsyn.org/orgsyn/pdfs/CV6P0869.pdf] :(CH2S)3 + RLi → (CH2S)2(CHLiS) + RH:(CH2S)2(CHLiS) + R’Br → (CH2S)2(CHR’S) + LiBr:(CH2S)2(CHR’S) + H2O → R’CHO + ….Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above.

It is also a precursor to other organosulfur reagents. For example, chlorination in the presence of water affords the chloromethylsulfonyl chloride: [Paquette, L. A.; Wittenbrook, L. S. “2-Chlorothiirane 1,1-Dioxide” Organic Syntheses, Collected Volume 5, p.231 (1973). http://www.orgsyn.org/orgsyn/pdfs/CV5P0231.pdf] :(CH2S)3 + 9 Cl2 + 6 H2O → 3 ClCH2SO2Cl + 12 HCl

References


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