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798851

Sigma-Aldrich

SnAP 2Me-M Reagent

Sinonimo/i:

2-[(Tributylstannyl)methoxy]-1-propanamine

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About This Item

Formula empirica (notazione di Hill):
C16H37NOSn
Numero CAS:
1557288-07-9
Peso molecolare:
378.18
Codice UNSPSC:
12352103
ID PubChem:
329768675

Descrizione

Flash point (deg F): >230

Forma fisica

liquid

Indice di rifrazione

n/D 1.487

Densità

1.128 at 25 °C

Temperatura di conservazione

−20°C

Stringa SMILE

CCCC[Sn](CCCC)(COC(C)CN)CCCC

InChI

1S/C4H10NO.3C4H9.Sn/c1-4(3-5)6-2;3*1-3-4-2;/h4H,2-3,5H2,1H3;3*1,3-4H2,2H3;
MALMPZOIHFDDCK-UHFFFAOYSA-N

Applicazioni

SnAP Reagents provide a one-step route, in tandem with various aldehyde substrates, to saturated N-heterocycles. The synthesis of N-heterocycles through SnAP Reagents requires mild reaction conditions, and aldehydes bearing aryl, heteroaryl, glyoxyl, aliphatic, and halogenated groups are well tolerated. This product was introduced in collaboration with the Bode Research Group

Automate your N-heterocycle formation with Synple Automated Synthesis Platform (SYNPLE-SC002)

Altre note

Technology spotlight: SnAP Reagents
Professor product portal: Jeffrey Bode Research Group
SnAP Reagents for the Synthesis of Piperazines and Morpholines
SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes
SnAP Reagents for a Cross-Coupling Approach to the One-Step Synthesis of Saturated N-Heterocycles

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Avvertenze

Danger

Classi di pericolo

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT RE 1

Codice della classe di stoccaggio

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
MKCD6831
MKCC8440
MKBZ4439V
MKBV5350V

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Michael U Luescher et al.
Organic letters, 16(4), 1236-1239 (2014-02-08)
Substituted piperazines and morpholines are valuable structural motifs in biologically active compounds, but are not easily prepared by contemporary cross-coupling approaches. In this report, we introduce SnAP reagents for the transformation of aldehydes into N-unprotected piperazines and morpholines. This approach
Woon-Yew Siau et al.
Journal of the American Chemical Society, 136(51), 17726-17729 (2014-12-09)
The combination of cyclic ketones and stannyl amine protocol (SnAP) reagents affords saturated, spirocyclic N-heterocycles under operationally simple reaction conditions. The resulting, N-unprotected spirocyclic amines are in great demand as scaffolds for drug discovery and development. The union of SnAP
Cam-Van T Vo et al.
Nature chemistry, 6(4), 310-314 (2014-03-22)
Interest in saturated N-heterocycles as scaffolds for the synthesis of bioactive molecules is increasing. Reliable and predictable synthetic methods for the preparation of these compounds, especially medium-sized rings, are limited. We describe the development of SnAP (Sn amino protocol) reagents
SnAP reagents for the transformation of aldehydes into substituted thiomorpholines--an alternative to cross-coupling with saturated heterocycles.
Cam-Van T Vo et al.
Angewandte Chemie (International ed. in English), 52(6), 1705-1708 (2013-01-03)

Protocolli

SnAP Reagents

Saturated N-heterocyclic building blocks or SnAP Reagents are of growing importance for the convenient synthesis of medium-ring saturated N-heterocycles, including bicyclic and spirocyclic structures. SnAP reagents are stable and readily available and can be coupled with widely available aromatic, heteroaromatic, aliphatic, and glyoxylic aldehydes.

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