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
CAS Number	290-57-3 1,2: 11084-06-3 1,3: 27813-20-3
3D model (JSmol)	1,2: Interactive image 1,3: Interactive image 1,4: Interactive image
ChemSpider	1,2: 10609054 1,3: 10609007 1,4: 10465777
PubChem CID	1,2: 15789245 1,3: 15789246 1,4: 15789247
CompTox Dashboard (EPA)	1,2: DTXSID50911874 1,3: DTXSID50578325
InChI 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
SMILES 1,2: C1=CNSC=C1 1,3: C1N=CC=CS1 1,4: C\1=C\N\C=C/S/1
Properties
Chemical formula	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). Y verify (what is YN ?) 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.

Tautomers

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

See also

• Methylene blue, contains a related ring with nitrogen and a positively charged sulfur atom
• Phenothiazine, a thiazine fused with two benzene rings
• Thiomorpholine, a saturated analog of thiazine

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.