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900814 Sigma-Aldrich

SLAP TM

≥95%

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

  • CAS Number 1226877-72-0

  • Empirical Formula (Hill Notation) C6H17NSSi

  • Molecular Weight 163.36

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Properties

Related Categories Chemical Synthesis, Organometallic Reagents, Organosilicon, Other Organosilicon, SLAP Reagents More...
assay   ≥95%
form   liquid
refractive index   n/D 1.4811
density   0.90746 g/mL
storage temp.   2-8°C

Description

Packaging

500 mg in glass insert

Application

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.

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

RIDADR 
NONH for all modes of transport

Documents

Certificate of Analysis

Protocols & Articles

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
15

References

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