:Thietane

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470606627

| ImageFileL1 = Thietane2.svg

| ImageFileL1_Ref = {{Chemboximage|correct|??}}

| ImageSizeL1 = 80

| ImageAltL1 = Structural formula of thietane

| ImageFileR1 = Thietane 3D ball.png

| ImageSizeR1 = 125

| ImageAltR1 = Ball-and-stick model of the thietane molecule

| PIN= Thietane

|SystematicName = Thiacyclobutane

|OtherNames = Trimethylene sulfide

|Section1={{Chembox Identifiers

| CASNo = 287-27-4

| CASNo_Ref = {{cascite|correct|chemspider}}

| PubChem = 9251

| ChemSpiderID = 8895

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

| EINECS = 206-015-0

| UNNumber = 1993

| Beilstein = 102383

| UNII = 1O7C19QQDB

| ChEBI = 87565

| SMILES = C1CSC1

| StdInChI = 1S/C3H6S/c1-2-4-3-1/h1-3H2

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

| StdInChIKey = XSROQCDVUIHRSI-UHFFFAOYSA-N

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

}}

|Section2={{Chembox Properties

| C=3 | H=6 | S=1

| Appearance = Colourless liquid

| Odor = Sulfurous

| Density = 1.028 g cm⁻³

| BoilingPtC = 94 to 95}}

|Section3={{Chembox Hazards

| NFPA-H = 2

| NFPA-F = 4

| NFPA-R = 1

| FlashPt = −11(9) °C

| GHSPictograms = {{GHS02}} {{GHS07}}

| GHSSignalWord = DANGER

| HPhrases = {{H-phrases|225|302}}

| PPhrases = {{P-phrases|210}}

}}

|Section8={{Chembox Related

| OtherCompounds = Thiirane, Dithietane, Tetrahydrothiophene, Thiane, Thiepane, Thiocane, Thionane

| OtherAnions = Oxetane, Azetidine, Phosphetane

}}

}}

Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom.{{cite journal |last= Leśniak |first=S |author2=Lewkowski, J |author3=Kudelska, W |author4= Zając, A | title =Thietanes and Thietes: Monocyclic |journal =Comprehensive Heterocyclic Chemistry III |year=2008 |volume=2 |issue=7 |pages=389–428 |doi=10.1016/B978-008044992-0.00207-8}}{{cite journal |last=Block |first=E |author2=DeWang, M | title =Thietanes and Thietes: Monocyclic |journal =Comprehensive Heterocyclic Chemistry II |year=1996 |volume=1 |issue=24 |pages=773–802 |doi=10.1016/B978-008096518-5.00024-1}} Some derivatives are of interest as drugs.{{cite journal |doi=10.2174/1568026622666220511154228 |title=Thietanes and Derivatives thereof in Medicinal Chemistry |date=2022 |last1=Francisco |first1=Karol R. |last2=Ballatore |first2=Carlo |journal=Current Topics in Medicinal Chemistry |volume=22 |issue=15 |pages=1219–1234 |pmid=35546768 }}

Thietane, and its derivative 2-propylthietane, are strong-smelling mouse alarm pheromones and predator scent analogues.{{cite journal |last1 = Sievert | first1 = Thorbjörn | last2 = Laska | first2 = Matthias | year = 2016|title = Behavioral responses of CD-1 mice to six predator odor components| journal = Chem. Senses| volume = 41 | issue = 5| pages = 399–406 |doi=10.1093/chemse/bjw015| pmid=26892309| doi-access = free}}{{cite journal |last1 = Brechbuhl | first1 = J | last2 = Moine | first2 = F|last3 = Klaey | first3 = M | last4 = Nenniger-Tosato | first4 = M|last5 = Hurni | first5 = N | last6 = Sporkert | first6 = F|last7 = Giroud | first7 = C | last8 = Broillet | first8 = MC | year = 2013|title = Mouse alarm pheromone shares structural similarity with predator scents| journal = Proc. Natl. Acad. Sci. U.S.A.| volume = 110 | issue = 12| pages = 4762–4767 |doi=10.1073/pnas.1214249110| pmid=23487748 | pmc=3607058| bibcode = 2013PNAS..110.4762B | doi-access = free}} Both the mouse and human olfactory receptors MOR244-3 and OR2T11, respectively, were found to respond to thietane in the presence of copper.{{cite journal | last1 = Li | first1 = Shengju | last2 = Ahmed | first2 = Lucky | last3 = Zhang | first3 = Ruina | last4 = Pan | first4 = Yi | last5 = Matsunami | first5 = Hiroaki | last6 = Burger | first6 = Jessica L | last7 = Block | first7 = Eric | last8 = Batista | first8 = Victor S | last9 = Zhuang | first9 = Hanyi | year = 2016|title = Smelling sulfur: Copper and silver regulate the response of human odorant receptor OR2T11 to low molecular weight thiols| journal = Journal of the American Chemical Society | volume = 138 | issue = 40 | doi=10.1021/jacs.6b06983 | pmid=27659093 | pages=13281–13288| bibcode = 2016JAChS.13813281L }}