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900399

Sigma-Aldrich

SLAP N-Bn Pip Reagent

95%

Synonym(s):

N1-Benzyl-N1-((trimethylsilyl)methyl)ethane-1,2-diamine

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About This Item

Empirical Formula (Hill Notation):
C13H24N2Si
CAS Number:
1908469-38-4
Molecular Weight:
236.43
UNSPSC Code:
12352200
PubChem Substance ID:
329769827
NACRES:
NA.22

Quality Level

100

assay

95%

form

liquid (paste)

refractive index

n/D 1.5071

density

0.9366 g/mL

storage temp.

−20°C

Related Categories

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

198.0 °F

flash_point_c

92.2 °C

Certificates of Analysis (COA)

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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

Protocols

Saturated N-heterocyclic (SnAP) Reagents

The Bode group has developed SnAP (stannyl amine protocol) reagents that cross-couple with aldehydes and ketones to provide one-step access to a wide variety of saturated N-heterocycles.

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