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900404

Sigma-Aldrich

SLAP HydroPyridopyrazine Reagent

≥95%

Synonym(s):

(1-((Trimethylsilyl)methyl)piperidin-2-yl)methanamine

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About This Item

Empirical Formula (Hill Notation):
C10H24N2Si
CAS Number:
2023645-22-7
Molecular Weight:
200.40
UNSPSC Code:
12352103
PubChem Substance ID:
329769829
NACRES:
NA.22

assay

≥95%

form

liquid

refractive index

n/D 1.4470

density

0.9030 g/mL

storage temp.

−20°C

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

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pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

175.0 °F

flash_point_c

79.44 °C

Certificates of Analysis (COA)

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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
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
Per Haberkant et al.
Biochimica et biophysica acta, 1841(8), 1022-1030 (2014-01-21)
Understanding biological processes at the mechanistic level requires a systematic charting of the physical and functional links between all cellular components. While protein-protein and protein-nucleic acid networks have been subject to many global surveys, other critical cellular components such as
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
In vivo profiling and visualization of cellular protein-lipid interactions using bifunctional fatty acids.
Per Haberkant et al.
Angewandte Chemie (International ed. in English), 52(14), 4033-4038 (2013-03-02)

Protocols

SiLicon Amine Protocol (SLAP) Reagents

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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