900815

SLAP 5-TMS TM

≥95%

• Synonym(s): 2-((Bis(trimethylsilyl)methyl)thio)ethanamine
• Empirical Formula (Hill Notation): C₉H₂₅NSSi₂
• CAS Number: 2084112-39-8
• Molecular Weight: 235.54
• UNSPSC Code: 12352200
• NACRES: NA.22

Properties

• Assay: ≥95%
• form: suspension
• density: 0.9126
• storage temp.: 2-8°C
• SMILES string: NCCSC([Si](C)(C)C)[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

• Pictograms: GHS02
• Signal Word: Danger
• Hazard Statements: H225
• Precautionary Statements: P210 - P370 + P378 - P403 + P235
• Hazard Classifications: Flam. Liq. 2
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 30.0 °F
• Flash Point(C): -1.11 °C