1,4-Oxathiane

1,4-Oxathiane
Names
	Preferred IUPAC name 1,4-Oxathiane
	Other names 1,4-Thioxane;p-Thioxane; 1-Oxa-4-thiacyclohexane
Identifiers
CAS Number	15980-15-1;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.036.454
EC Number	240-117-6;
PubChemCID	27596;
UNII	2X66H33V2V;
CompTox Dashboard(EPA)	DTXSID0065985;
	InChI InChI=1S/C4H8OS/c1-3-6-4-2-5-1/h1-4H2 Key: JBYHSSAVUBIJMK-UHFFFAOYSA-N;
	SMILES C1CSCCO1;
Properties
Chemical formula	C4H8OS
Molar mass	104.17g·mol−1
Melting point	−17 °C (1 °F; 256 K)
Boiling point	147.0 °C (296.6 °F; 420.1 K)
Hazards
	GHSlabelling:
Pictograms
Signal word	Warning
Hazard statements	H226,H315,H319,H335
Precautionary statements	P210,P233,P240,P241,P242,P243,P261,P264,P271,P280,P302+P352,P303+P361+P353,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P370+P378,P403+P233,P403+P235,P405,P501
	Lethal doseor concentration (LD, LC):
LD50(median dose)	2830 mg/kg oral rat
Related compounds
Related compounds	1,4-dioxane
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). Infobox references

1,4-Oxathianeis aheterocyclic compoundcontaining oneoxygenatom and onesulfuratom at opposite corners of asaturatedsix-membered ring. Bysystematic numbering,the oxygen atom is position number 1, sulfur is number 4, and positions 2, 3, 5, and 6 arecarbonatoms.

Production

1,4-Oxathiane can be produced from low cost ingredients by heatingethylene glycolorethylene oxidewithhydrogen sulfide.Alternate ways are to dehydrate bis(hydroxy ethyl) sulfide by heating withpotassium hydrogen sulfate.These reactions also form 1,4-dithianeas abyproduct.^[1]

The original 1912 preparation of 1,4-oxathiane involved iodoethyl ether with potassium sulfide in alcohol. A similar method used 2-chloroethyl ether.^[1]

Reactions

The sulfur atom in 1,4-oxathiane can undergo reaction as other substituted sulfides can. It can be oxidised to asulfoxidewithcalcium hypochloriteorsodium periodate,^[2]or continuing to asulfone.

It can react with ammonia to form diimines.^[3]

With elementalchlorinebelow 0 °C, 3-chloro-1,4-oxathiane is formed. Above 0 °C, 2,3-dichloro-1,4-oxathiane results and further chlorination yields 2,3,5,6-tetrachloro-1,4-oxathiane.^[1]

Withhydrofluoric acid,1,4-oxathiane is undergoeselectrophilic fluorinationto yield perfluoro-1,4-oxathiane: all eight hydrogen atoms are replaced with fluorinesubstituents,and also four fluorine atoms are attached to the sulfur atom.^[1]

With elementalbrominein ether, an oxathianium salt is formed. In this an extra bromine atom bonds to the sulfur atom which gets a positive charge. To balance this, a bromide ion forms to make up a salt. Similarly iodine in acetic acid reacts to make 4-iodo-1,4-oxathianium iodide. Heating 1,4-oxathiane withethyl iodideyields 4-ethyl-1,4-oxathianium iodide.^[1]

References

^^a ^b ^c ^d ^eBreslow, David S.;Skolnik, Herman (2009).Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles.John Wiley & Sons. pp. 823–828.ISBN 978-0-470-18833-0.
^Yamamoto, ed. (2004). "Product Subclass 8: Aluminum Oxide (Alumina)".Category 1, Organometallics.doi:10.1055/sos-SD-007-00192.ISBN 9783131122117.
^Kambe, ed. (2008). "Product Subclass 2: Cyclic Dialkyl Sulfones and Derivatives".Category 5, Compounds with One Saturated Carbon Heteroatom Bond.doi:10.1055/sos-SD-039-00922.ISBN 9783131189219.

[multi-1] Breslow, David S.;Skolnik, Herman (2009).Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles.John Wiley & Sons. pp. 823–828.ISBN 978-0-470-18833-0.

[2] Yamamoto, ed. (2004). "Product Subclass 8: Aluminum Oxide (Alumina)".Category 1, Organometallics.doi:10.1055/sos-SD-007-00192.ISBN 9783131122117.

[3] Kambe, ed. (2008). "Product Subclass 2: Cyclic Dialkyl Sulfones and Derivatives".Category 5, Compounds with One Saturated Carbon Heteroatom Bond.doi:10.1055/sos-SD-039-00922.ISBN 9783131189219.

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