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798851

Sigma-Aldrich

SnAP 2Me-M Reagent

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C16H37NOSn
Numéro CAS:
1557288-07-9
Poids moléculaire :
378.18
Code UNSPSC :
12352103
ID de substance PubChem :
329768675

Description

Flash point (deg F): >230

Forme

liquid

Indice de réfraction

n/D 1.487

Densité

1.128 at 25 °C

Température de stockage

−20°C

Chaîne SMILES 

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;

Clé InChI

MALMPZOIHFDDCK-UHFFFAOYSA-N

Application

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)

Autres remarques

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

798916

SnAP OA Reagent

798908

SnAP Pip Reagent

798894

SnAP DA Reagent

798886

SnAP TM Reagent

798878

SnAP M Reagent, 95%

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

900402

SLAP HydroQuinoxaline, 95%

900401

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

900403

SLAP HydroPyrrolopyrazine Reagent

900406

SLAP N-Bn-3Me-Pip Reagent

900755

SLAP TA, 95%

900756

SLAP M, ≥95%

900814

SLAP TM, ≥95%

900815

SLAP 5-TMS TM, ≥95%

Pictogrammes

Skull and crossbonesHealth hazardEnvironment
GHS06,GHS08,GHS09

Mention d'avertissement

Danger

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
MKCD6831
MKCC8440
MKBZ4439V
MKBV5350V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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)

Protocoles

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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