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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

functional group

amine

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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SnAP 2Me-M Reagent

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SnAP 3Me-M Reagent

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SnAP 2-Spiro-(4-Pip) M Reagent

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SnAP 3-Spiro-(4-Pip) M Reagent

804177

SnAP 3-Spiro-(2-Pyr) M Reagent

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SnAP 2-Spiro-(2-Pyr) M Reagent

804150

SnAP 2,3-Bicyclo-(3,4-Pyr) M Reagent

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SLAP HydroQuinoxaline, 95%

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SLAP 2,3-Bicyclo-(3,4-THF) N-BnPip Reagent, ≥95%

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900755

SLAP TA, 95%

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900814

SLAP TM, ≥95%

900815

SLAP 5-TMS TM, ≥95%

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

175.0 °F

Flash Point(C)

79.44 °C

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Certificates of Analysis (COA)

Lot/Batch Number
MKCB4107

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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
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
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
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)
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

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.

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.

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.

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.

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