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Documentos Principais

900755

Sigma-Aldrich

SLAP TA

95%

Sinônimo(s):

3-(((Trimethylsilyl)methyl)thio)propan-1-amine

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About This Item

Fórmula empírica (Notação de Hill):
C7H19NSSi
Número CAS:
Peso molecular:
177.38
Número MDL:
Código UNSPSC:
12352103
NACRES:
NA.22

Nível de qualidade

Ensaio

95%

Formulário

liquid

densidade

0.90452

grupo funcional

amine
thioether

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

[Si](CSCCCN)(C)(C)C

InChI

1S/C7H19NSSi/c1-10(2,3)7-9-6-4-5-8/h4-8H2,1-3H3

chave InChI

CNESDLLESCAVSR-UHFFFAOYSA-N

Aplicação

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.

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Pictogramas

Flame

Palavra indicadora

Warning

Frases de perigo

Declarações de precaução

Classificações de perigo

Flam. Liq. 3

Código de classe de armazenamento

3 - Flammable liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

75.0 °F

Ponto de fulgor (°C)

23.89 °C


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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

Protocolos

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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