Thiomorpholine
{{Short description|Chemical compound}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470607284
| Name = Thiomorpholine
| ImageFileL1 = Thiomorpholine numbering.svg
| ImageSizeL1 = 100px
| ImageNameL1 = Thiomorpholine
| ImageFileR1 = Thiomorpholine-3D-balls.png
| ImageSizeR1 = 120px
| ImageName1 = Thiomorpholine
| PIN = Thiomorpholine{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=142 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}
| OtherNames = Thiamorpholine
|Section1={{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 36392
| SMILES = S1CCNCC1
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 60509
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2333141
| PubChem = 67164
| InChI = 1/C4H9NS/c1-3-6-4-2-5-1/h5H,1-4H2
| InChIKey = BRNULMACUQOKMR-UHFFFAOYAQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H9NS/c1-3-6-4-2-5-1/h5H,1-4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BRNULMACUQOKMR-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 123-90-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3A8R61G6QV
| RTECS =
}}
|Section2={{Chembox Properties
| C=4 | H=9 | N=1 | S=1
| Appearance = Colorless liquid
| Odor = Strong odor resembling piperidineMerck Index, 12th Edition, monograph 9435, p. 1587
| Density = 1.0882 g/cm3
| MeltingPtC =
| BoilingPtC = 169
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Thiomorpholine, {{chem2|HN(CH2)4S}}, is a heterocyclic compound containing nitrogen and sulfur. It can be considered a thio analog of morpholine.
It can be prepared from cysteamine and vinyl chloride:{{cite journal |doi=10.1021/acs.oprd.2c00214 |title=Synthesis of Thiomorpholine via a Telescoped Photochemical Thiol–Ene/Cyclization Sequence in Continuous Flow |date=2022 |last1=Steiner |first1=Alexander |last2=Nelson |first2=Ryan C. |last3=Dallinger |first3=Doris |last4=Kappe |first4=C. Oliver |journal=Organic Process Research & Development |volume=26 |issue=8 |pages=2532–2539 |pmid=36032361 |pmc=9396661 }}
: {{chem2|H2NCH2CH2SH + CH2\dCHCl -> HN(CH2)4S + HCl}}