Tris(tert-butoxy)silanethiol

Tris(tert-butoxy)silanethiol is a silicon compound containing three tert-butoxy groups and a rare Si–S–H functional group. This colourless compound serves as a hydrogen donor in radical chain reactions. It was first prepared by alcoholysis of silicon disulfide and purified by distillation:^[1]

3 (CH₃)₃COH + SiS₂ → [(CH₃)₃CO]₃SiSH + H₂S

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Tris(tert-butoxy)silanethiol

Names
Preferred IUPAC name Tri-tert-butoxysilanethiol
Other names Tri(tert-butoxy)silanethiol
Identifiers
CAS Number	690-52-8 N
3D model (JSmol)	Interactive image
Abbreviations	TBST
ChemSpider	4414610 Y
PubChem CID	5246420
CompTox Dashboard (EPA)	DTXSID50412972
InChI InChI=1S/C12H28O3SSi/c1-10(2,3)13-17(16,14-11(4,5)6)15-12(7,8)9/h16H,1-9H3 Key: ZVUGYOCGLCLJAV-UHFFFAOYSA-N
SMILES CC(C)(C)O[Si](S)(OC(C)(C)C)OC(C)(C)C
Properties
Chemical formula	C12H28O3SSi
Molar mass	280.50 g·mol−1
Appearance	Colourless liquid
Boiling point	113 to 115 °C (235 to 239 °F; 386 to 388 K) at 35 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Since 1962 it was thoroughly studied including its acid-base properties^[2][3] and coordination chemistry with metal ions. It coordinates to metal ions via the sulfur and oxygen donor atoms.^{[4][5][6][7][8][9]}