Author:
Ding Mingyan,Willis Michael
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
.