Wiley
,  pages 1-3

N ‐Sulfinyltriisopropylsilylamine

Mingyan Ding
, 
Michael Willis
Publication type: Other
Publication date: 2024-07-17
Wiley
Abstract

image
[2762957‐87‐7] C 9 H 21 NOSSi (MW 219.4)

InChI =  1S/C9H21NOSSi/c1‐7(2)13(8(3)4,9(5)6)10‐12‐11/h7‐9H,1‐6H3

InChIKey =  ZJJCFIWQFNLRFK‐UHFFFAOYSA‐N

(used as a sulfinamidation or a sulfinamidination reagent for the synthesis of aza‐sulfur compounds)

  • Alternative Names : triisopropylsilyl sulfinamine, ((triisopropylsilyl)imino)‐λ 4 ‐sulfanone, TIPS ‐ NSO.

  • Physical Data : unknown.

  • Solubility : miscible with common organic solvents including THF, Et 2 O, CH 2 Cl 2 , CHCl 3 , MeCN, toluene, and benzene.

  • Form Supplied in : light‐yellow liquid, commercially available.

  • Analysis of Reagent Purity : spectroscopic data: IR, NMR ( 1 H, 13 C). 1

  • Preparative Method : TIPS ‐ NSO is prepared from dropwise addition of SOCl 2 to TIPS‐NH 2 in the presence of Et 3 N at 0 °C in anhydrous Et 2 O. After stirring the reaction for 2 h, the solid Et 3 N·HCl salt is removed by filtration through a pad of anhydrous Na 2 SO 4 and the removal of the solvent in vacuo affords TIPS‐NSO. 1

  • Purification : none required.

  • Handling, Storage, and Precautions : TIPS ‐ NSO may be slightly volatile. For this reason, when removing solvent on a rotary evaporator, the bath temperature should be set to 30 °C or lower. For long‐term storage, it is kept at −20 °C in a freezer under an inert atmosphere. Hydrolysis of TIPS‐NSO can potentially result in the evolution of toxic SO 2 .

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