900814

SLAP TM

≥95%

• Synonym(s): 2-(((Trimethylsilyl)methyl)thio)ethanamine
• Empirical Formula (Hill Notation): C₆H₁₇NSSi
• CAS Number: 1226877-72-0
• Molecular Weight: 163.36
• UNSPSC Code: 12352200
• NACRES: NA.22

Properties

• Assay: ≥95%
• form: liquid
• refractive index: n/D 1.4811
• density: 0.90746 g/mL
• functional group: amine; thioether
• storage temp.: 2-8°C
• SMILES string: NCCSC[Si](C)(C)C

Description

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 Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 174.0 °F
• Flash Point(C): 78.89 °C