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900815

Sigma-Aldrich

SLAP 5-TMS TM

≥95%

Sinónimos:

2-((Bis(trimethylsilyl)methyl)thio)ethanamine

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About This Item

Fórmula empírica (notación de Hill):
C9H25NSSi2
Número de CAS:
2084112-39-8
Peso molecular:
235.54
UNSPSC Code:
12352200
NACRES:
NA.22

assay

≥95%

form

suspension

density

0.9126

storage temp.

2-8°C

SMILES string

NCCSC([Si](C)(C)C)[Si](C)(C)C

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

Related product

Referencia del producto
Descripción
Precios

798916

SnAP OA Reagent

798908

SnAP Pip Reagent

798894

SnAP DA Reagent

798886

SnAP TM Reagent

798878

SnAP M Reagent, 95%

798851

SnAP 2Me-M Reagent

798843

SnAP 3Me-M Reagent

804088

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

804142

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

804177

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

804185

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

804150

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

900404

SLAP HydroPyridopyrazine Reagent, ≥95%

900402

SLAP HydroQuinoxaline, 95%

900401

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

900403

SLAP HydroPyrrolopyrazine Reagent

900400

SLAP 3-SpiroCyHex N-Bn Pip Reagent, ≥95%

900399

SLAP N-Bn Pip Reagent, 95%

900406

SLAP N-Bn-3Me-Pip Reagent

900755

SLAP TA, 95%

900756

SLAP M, ≥95%

900814

SLAP TM, ≥95%

pictograms

Flame
GHS02

signalword

Danger

hcodes

H225

Hazard Classifications

Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

30.0 °F

flash_point_c

-1.11 °C

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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
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

Protocolos

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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