Thiomorpholine

Thiomorpholine, .mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-s

Thiomorpholine
Thiomorpholine
Thiomorpholine
Thiomorpholine
Names
Preferred IUPAC name
Thiomorpholine[1]
Other names
Thiamorpholine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.238 Edit this at Wikidata
UNII
  • InChI=1S/C4H9NS/c1-3-6-4-2-5-1/h5H,1-4H2 checkY
    Key: BRNULMACUQOKMR-UHFFFAOYSA-N checkY
  • InChI=1/C4H9NS/c1-3-6-4-2-5-1/h5H,1-4H2
    Key: BRNULMACUQOKMR-UHFFFAOYAQ
  • S1CCNCC1
Properties
C4H9NS
Molar mass 103.18 g·mol−1
Appearance Colorless liquid
Odor Strong odor resembling piperidine[2]
Density 1.0882 g/cm3
Boiling point 169 °C (336 °F; 442 K)[2]
Miscible[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

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

  1. ^ 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.
  2. ^ a b c Merck Index, 12th Edition, monograph 9435, p. 1587
  3. ^ 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.


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