Thiomorpholine

Thiomorpholine
Thiomorpholine source ↗	source ↗
Names
	Preferred IUPAC name Thiomorpholine
	Other names Thiamorpholine
Identifiers
CAS Number	123-90-0 Y;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36392 Y;
ChEMBL	ChEMBL2333141 N;
ChemSpider	60509 Y;
ECHA InfoCard	100.004.238
PubChem CID	67164;
UNII	3A8R61G6QV Y;
CompTox Dashboard (EPA)	DTXSID80153826 ;
	InChI InChI=1S/C4H9NS/c1-3-6-4-2-5-1/h5H,1-4H2 Y Key: BRNULMACUQOKMR-UHFFFAOYSA-N Y; InChI=1/C4H9NS/c1-3-6-4-2-5-1/h5H,1-4H2 Key: BRNULMACUQOKMR-UHFFFAOYAQ;
	SMILES S1CCNCC1;
Properties
Chemical formula	C4H9NS
Molar mass	103.18 g·mol−1
Appearance	Colorless liquid
Odor	Strong odor resembling piperidine
Density	1.0882 g/cm3
Boiling point	169 °C (336 °F; 442 K)
Solubility in water	Miscible
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Thiomorpholine, 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:³

H₂NCH₂CH₂SH + CH₂=CHCl → HN(CH₂)₄S + HCl

References

International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 142. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
Merck Index, 12th Edition, monograph 9435, p. 1587
Steiner, Alexander; Nelson, Ryan C.; Dallinger, Doris; Kappe, C. Oliver (2022). "Synthesis of Thiomorpholine via a Telescoped Photochemical Thiol–Ene/Cyclization Sequence in Continuous Flow". Organic Process Research & Development. 26 (8): 2532–2539. doi:10.1021/acs.oprd.2c00214. PMC 9396661. PMID 36032361.