:1,3,5-Trithiane

{{short description|Chemical compound}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477204831

| ImageFile1_Ref = {{chemboximage|correct|??}}

| 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

| PIN = 1,3,5-Trithiane

| OtherNames = Thioformaldehyde trimer, Trimethylentrisulfide, Trimethylene trisulfide, Trithioformaldehyde, 1,3,5-Trithiacyclohexane, sym-Trithiane, Thioform, s-Trithiane

|Section1={{Chembox Identifiers

| InChI = 1/C3H6S3/c1-4-2-6-3-5-1/h1-3H2

| InChIKey = LORRLQMLLQLPSJ-UHFFFAOYAA

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C3H6S3/c1-4-2-6-3-5-1/h1-3H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LORRLQMLLQLPSJ-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 291-21-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4AM764YC6X

| EINECS = 206-029-7

| PubChem = 9264

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 39196

| ChemSpiderID = 8907

| SMILES = S1CSCSC1

}}

|Section2={{Chembox Properties

| Formula = C{{sub|3}}H{{sub|6}}S{{sub|3}}

| MolarMass = 138.27

| Appearance = Colourless solid

| Density = 1.6374 g/cm{{sup|3}}David R. Lide, ed. Handbook of Chemistry and Physics, 85th Edition, Internet Version 2005. CRC Press, 2005.

| MeltingPtC = 215 to 220

| MeltingPt_notes =

| BoilingPt =

| Solubility = Slightly soluble

| SolubleOther = Benzene

}}

|Section3={{Chembox Hazards

| MainHazards = Toxic (T)

| NFPA-H = 1

| NFPA-F = 1

| NFPA-R = 0

| NFPA-S =

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|319}}

| PPhrases = {{P-phrases|264|280|305+351+338|313}}

| FlashPt =

| AutoignitionPt =

}}

}}

1,3,5-Trithiane is the chemical compound with the formula (CH{{sub|2}}S){{sub|3}}. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges 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://orgsyn.org/Content/pdfs/procedures/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 can be alkylated.Seebach, D.; Beck, A. K. "Aldehydes From sym-Ttrithiane: n-Pentadecanal" Organic Syntheses, Collected Volume 6, p.869 (1988). http://orgsyn.org/Content/pdfs/procedures/CV6P0869.pdf

:(CH{{sub|2}}S){{sub|3}} + RLi → (CH{{sub|2}}S){{sub|2}}(CHLiS) + RH

:(CH{{sub|2}}S){{sub|2}}(CHLiS) + R{{prime}}Br → (CH{{sub|2}}S){{sub|2}}(CHR{{prime}}S) + LiBr

:(CH{{sub|2}}S){{sub|2}}(CHR{{prime}}S) + H{{sub|2}}O → R{{prime}}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 chloromethyl sulfonyl chloride:Paquette, L. A.; Wittenbrook, L. S. "2-Chlorothiirane 1,1-Dioxide" Organic Syntheses, Collected Volume 5, p.231 (1973). http://orgsyn.org/Content/pdfs/procedures/CV5P0231.pdf

:(CH{{sub|2}}S){{sub|3}} + 9 Cl{{sub|2}} + 6 H{{sub|2}}O → 3 ClCH{{sub|2}}SO{{sub|2}}Cl + 12 HCl

image:SymTrithiane.jpg