900755
SLAP TA
95%
Synonym(s):
3-(((Trimethylsilyl)methyl)thio)propan-1-amine
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About This Item
Empirical Formula (Hill Notation):
C7H19NSSi
CAS Number:
Molecular Weight:
177.38
MDL number:
UNSPSC Code:
12352103
NACRES:
NA.22
Quality Level
assay
95%
form
liquid
density
0.90452
functional group
amine, thioether
storage temp.
2-8°C
SMILES string
[Si](CSCCCN)(C)(C)C
InChI
1S/C7H19NSSi/c1-10(2,3)7-9-6-4-5-8/h4-8H2,1-3H3
InChI key
CNESDLLESCAVSR-UHFFFAOYSA-N
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
signalword
Warning
hcodes
pcodes
Hazard Classifications
Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
75.0 °F
flash_point_c
23.89 °C
Regulatory Information
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Protocols
The expanding class of SLAP reagents provides access to saturated N-heterocycles and aliphatic aldehydes and ketones without additional reagents or the generation of toxic byproducts.
Moritz K Jackl et al.
Organic letters, 19(17), 4696-4699 (2017-08-17)
Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic
Sheng-Ying Hsieh et al.
Organic letters, 18(9), 2098-2101 (2016-04-22)
Silicon amine protocol (SLAP) reagents for photocatalytic cross-coupling with aldehydes and ketones to form N-unprotected piperazines have been developed. This blue light promoted process tolerates a wide range of heteroaromatic, aromatic, and aliphatic aldehydes and structurally and stereochemically complex SLAP
Sheng-Ying Hsieh et al.
ACS central science, 3(1), 66-72 (2017-02-06)
Redox neutral photocatalytic transformations often require careful pairing of the substrates and photoredox catalysts in order to achieve a catalytic cycle. This can limit the range of viable transformations, as we recently observed in attempting to extend the scope of
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 900755-500MG | 04061833251010 |