Thiazine

Thiazine /ˈθaɪəziːn/ is an organic compound containing a ring of four carbon, one nitrogen and one sulfur atom. There are three isomers of thiazine, 1,2-thiazine, 1,3-thiazine, and 1,4-thiazine, which differ by the arrangement of the nitrogen and sulfur atoms in the ring.

1,4-Thiazine
Names
Preferred IUPAC name
4H-1,4-Thiazine
Other names
Parathiazine
Identifiers
3D model (JSmol)
ChemSpider
  • 1,2: InChI=1S/C4H5NS/c1-2-4-6-5-3-1/h1-5H
    Key: AGIJRRREJXSQJR-UHFFFAOYSA-N
  • 1,3: InChI=1S/C4H5NS/c1-2-5-4-6-3-1/h1-3H,4H2
    Key: NTYABNDBNKVWOO-UHFFFAOYSA-N
  • 1,4: InChI=1S/C4H5NS/c1-3-6-4-2-5-1/h1-5H
    Key: ZOXMLSDKXHNVOQ-UHFFFAOYSA-N
  • 1,2: C1=CNSC=C1
  • 1,3: C1N=CC=CS1
  • 1,4: C\1=C\N\C=C/S/1
Properties
C4H5NS
Molar mass 99.15 g·mol−1
Density 0.8465 g/cm3
Boiling point 76.5 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Derivatives of thiazine, often referred to as thiazines, are used for dyes, tranquilizers and insecticides.

Preparation

1,4-thiazine can be prepared from the corresponding dione using aluminium powder at high temperature.[1]

Synthesis of 1,4-thiazine.
Synthesis of 1,4-thiazine.

Tautomers

Three tautomers of 1,4-thiazine exist as above.

See also

References
  1. Barkenbus, Charles; Landis, Phillip S. (February 1948). "The Preparation of 1,4-Thiazine". Journal of the American Chemical Society. 70 (2): 684–685. doi:10.1021/ja01182a075. ISSN 0002-7863.
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