900814 Sigma-Aldrich



Synonym: 2-(((Trimethylsilyl)methyl)thio)ethanamine

  • CAS Number 1226877-72-0

  • Empirical Formula (Hill Notation) C6H17NSSi

  • Molecular Weight 163.36

  •  NACRES NA.22



Related Categories Chemical Synthesis, Organometallic Reagents, Organosilicon, Other Organosilicon, SLAP Reagents More...
Quality Level   100
assay   ≥95%
form   liquid
refractive index   n/D 1.4811
density   0.90746 g/mL
storage temp.   2-8°C
SMILES string   NCCSC[Si](C)(C)C



When used with aliphatic or aromatic aldehydes, this silicon amine protocol (SLAP) reagent enables the photomediated synthesis of thiomorpholines and thiazepanes. For photocatalytic cross-coupling with this SLAP Reagent, Ir[(ppy)2dtbbpy]PF6 ((747769) is used with a recommended starting combination of Lewis acids Bi(OTf)3 (633305) and Cu(OTf)2 (283673) prior to subsequent substrate-specific optimization. This product was introduced in collaboration with the Bode Research Group and provides a tin-free alternative to SnAP (tin amine protocol) reagents and is well-suited for scale-up reactions.


500 mg in glass insert

Other Notes

• Technology Spotlight: SLAP Reagents for Piperazine Synthesis
• Silicon Amine Reagents for the Photocatalytic Synthesis of Piperazines from Aldehydes and Ketones
• Lewis Acid Induced Toggle from Ir(II) to Ir(IV) Pathways in Photocatalytic Reactions: Synthesis of Thiomorpholines and Thiazepanes from Aldehydes and SLAP Reagents.
• Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis

Safety & Documentation

Safety Information

NONH for all modes of transport
WGK Germany 
Flash Point(F) 
174.0 °F
Flash Point(C) 
78.89 °C


Certificate of Analysis (COA)

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Protocols & Articles


Jeffrey Bode Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Jeffrey Bode Group – Professor Product Portal
Keywords: Annulations, Asymmetric synthesis, Catalysis, Cross couplings, transformation

SLAP Reagents for Piperazine Synthesis

The Bode group has recently developed and commercialized a number of SnAP (stannyl amine protocol) reagents that cross-couple with aldehydes and ketones to provide one-step access to a wide variety o...
Keywords: Building blocks, Chromatography, Column chromatography, Continuous flow chemistry, Cyclizations, Heterocycle formation, Infrared spectroscopy, Mass spectrometry, Solvents, transformation

Peer-Reviewed Papers


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