Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 1,3,5-Trithiane: Difference between pages

{{short description|Chemical compound}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477204831

| 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

| 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}}

| 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}}<ref name="crchcp">David R. Lide, ed. ''Handbook of Chemistry and Physics, 85th Edition'', Internet Version 2005. CRC Press, 2005.</ref>

| 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 [[chemical formula|formula]] (CH{{sub|2}}S){{sub|3}}. This [[heterocycle]] is the cyclic [[Trimer (chemistry)|trimer]] of the otherwise unstable species [[thioformaldehyde]]. It consists of a six-membered ring with alternating [[methylene bridge]]s and thioether groups. It is prepared by treatment of [[formaldehyde]] with [[hydrogen sulfide]].<ref>Bost, R. W.; Constable, E. W. "sym-Trithiane" Organic Syntheses, Collected Volume 2, p.610 (1943). http://orgsyn.org/Content/pdfs/procedures/CV2P0610.pdf</ref>

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 [[alkylate]]d.<ref>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</ref>

:(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 [[dithioacetal]]s undergo similar reactions to the above.

It is also a precursor to other [[organosulfur]] [[reagent]]s. For example, chlorination in the presence of water affords the chloromethyl [[sulfonyl chloride]]:<ref>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</ref>

:(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|thumb|left|200px|Sample of sym-trithiane.]]

==Trithianes==

Trithiane is the parent of a class of heterocycles called '''trithianes''', that formally result from substitution of various [[valence (chemistry)|monovalent]] [[functional group|groups]] for one or more of the hydrogen atoms. The species often arise from thiation of ketones and aldehydes. The incipient [[thioketone]]s and [[thioaldehyde]]s undergo [[Trimer (chemistry)|trimer]]ization. One example is [[2,2,4,4,6,6-hexamethyl-1,3,5-trithiane]], or trithioacetone, the trimer of [[thioacetone]] (propane-2-thione). Alternatively 1,3,5-trithiane can be deprotonated and alkylated to afford (SCH₂)_n(SCHR)_3-n.<ref>{{cite journal |doi=10.1002/recl.19931120611|title=Alkylation of the SCS linkage. Towards lipophilic mono- and ditopic heavy-metal receptors containing trithiane building blocks. Molecular structure of cis-2,4,6-tribenzyl-1,3,5-trithiane|year=2010|last1=Edema|first1=Jilles J. H.|last2=Hoogenraad|first2=Marcel|last3=Schoonbeek|first3=Franck S.|last4=Kellogg|first4=Richard M.|last5=Kooijman|first5=Huub|last6=Spek|first6=Anthony L.|journal=Recueil des Travaux Chimiques des Pays-Bas|volume=112|issue=6|pages=370–375}}</ref>

The conformation of trithianes has been well investigated.<ref>{{cite book|title=Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 2|volume=21|last1=Breslow |first1=David S. |author-link1=David S. Breslow |last2=Skolnik |first2= Herman |chapter=C3S3 Ring Systems|page=689|isbn=978-0-470-18833-0|year=2009|publisher=John Wiley & Sons }}</ref>

:[[File:ThioacetoneTrimer.svg|220px]]

==References==

<references/>

{{DEFAULTSORT:Trithiane, 1, 3, 5-}}

[[Category:Sulfur heterocycles]]

[[Category:Six-membered rings]]