Bis(trimethylsilyl)sulfur diimide

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
Names
Preferred IUPAC name
Bis(trimethylsilyl)-λ4-sulfanediimine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H18N2SSi2/c1-10(2,3)7-9-8-11(4,5)6/h1-6H3
    Key: JPAGRRHKURYWAM-UHFFFAOYSA-N
  • C[Si](C)(C)N=S=N[Si](C)(C)C
Properties
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:
GHS02: FlammableGHS07: Exclamation mark
Warning
H226, H319, H335
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).

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

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  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.