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900400 Sigma-Aldrich

SLAP 3-SpiroCyHex N-Bn Pip Reagent

≥95%

Synonym: 1-((Benzyl((trimethylsilyl)methyl)amino)methyl)cyclohexanamine

  • Empirical Formula (Hill Notation) C18H32N2Si

  • Molecular Weight 304.55

  •  PubChem Substance ID 329769828

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Properties

Related Categories Chemical Synthesis, Organometallic Reagents, Organosilicon, Other Organosilicon, SLAP Reagents More...
InChI Key   HHDPYUUHZQUCNL-UHFFFAOYSA-N
assay   ≥95%
form   liquid
refractive index   n/D 1.516
density   0.956 g/mL
storage temp.   −20°C

Description

Packaging

500 mg in glass bottle

Application

Silicon amine protocol (SLAP) reagents, in conjunction with aldehydes and ketones, form N-unprotected piperazines via photocatalytic cross-coupling with Ir[(ppy)2dtbbpy]PF6 (747769). Heteroaromatic, aromatic, and aliphatic aldehydes are well tolerated, as are structurally and stereochemically complex SLAP reagents. This product was introduced in collaboration with the Bode Research Group and provides a tin-free alternative to SnAP (tin amine protocol) reagents for piperazine synthesis.

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
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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