Bis(trimethylsilyl)sulfur diimide

Bis(trimethylsilyl)sulfur diimide
Names
	Preferred IUPAC name Bis(trimethylsilyl)-λ4-sulfanediimine
Identifiers
CAS Number	18156-25-7;
3D model (JSmol)	Interactive image;
ChemSpider	298617;
PubChem CID	336932;
CompTox Dashboard (EPA)	DTXSID00319982 ;
	InChI InChI=1S/C6H18N2SSi2/c1-10(2,3)7-9-8-11(4,5)6/h1-6H3 Key: JPAGRRHKURYWAM-UHFFFAOYSA-N;
	SMILES C[Si](C)(C)N=S=N[Si](C)(C)C;
Properties
Chemical formula	C6H18N2SSi2
Molar mass	206.45 g·mol−1
Appearance	colorless liquid
Density	0.877 g/cm3
Boiling point	59–61 °C (138–142 °F; 332–334 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bis(trimethylsilyl)sulfur diimide is the organosulfur compound with the formula S(NSiMe₃)₂ (Me = CH₃). A colorless liquid, it is a diaza analogue of sulfur dioxide, i.e., a sulfur diimide. It is a reagent in the synthesis of sulfur nitrides. For example, it is a precursor to C₂(N₂S)₂.^[1]

Bis(trimethylsilyl)sulfur diimide is prepared by the reaction of thionyl chloride and sodium bis(trimethylsilyl)amide:^[2]

SOCl₂ + 2 NaN(SiMe₃)₂ → S(NSiMe₃)₂ + 2 NaCl + O(SiMe₃)₂

References

^ Makarov, Alexander Yu.; Irtegova, Irina G.; Vasilieva, Nadezhda V.; Bagryanskaya, Irina Yu.; Borrmann, Tobias; Gatilov, Yuri V.; Lork, Enno; Mews, Ruediger; Stohrer, Wolf-Dieter; Zibarev, Andrey V. (2005). "[1,2,5]Thiadiazolo[3,4-c][1,2,5]thiadiazolidyl: A Long-Lived Radical Anion and Its Stable Salts". Inorganic Chemistry. 44 (20): 7194–7199. doi:10.1021/ic050583j. PMID 16180884.
^ Scherer, Otto J.; Wies, Reinhard (1970). "Synthese eines siliciumorganischen cyclischen Schwefeldiimids (Synthesis of an Organosilicon Cyclic Sulfur Diimide)". Zeitschrift für Naturforschung. 25B: 1486-7. doi:10.1515/znb-1970-1240. S2CID 93647579.

[1] Makarov, Alexander Yu.; Irtegova, Irina G.; Vasilieva, Nadezhda V.; Bagryanskaya, Irina Yu.; Borrmann, Tobias; Gatilov, Yuri V.; Lork, Enno; Mews, Ruediger; Stohrer, Wolf-Dieter; Zibarev, Andrey V. (2005). "[1,2,5]Thiadiazolo[3,4-c][1,2,5]thiadiazolidyl: A Long-Lived Radical Anion and Its Stable Salts". Inorganic Chemistry. 44 (20): 7194–7199. doi:10.1021/ic050583j. PMID 16180884.

[2] Scherer, Otto J.; Wies, Reinhard (1970). "Synthese eines siliciumorganischen cyclischen Schwefeldiimids (Synthesis of an Organosilicon Cyclic Sulfur Diimide)". Zeitschrift für Naturforschung. 25B: 1486-7. doi:10.1515/znb-1970-1240. S2CID 93647579.

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