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798908

Sigma-Aldrich

SnAP Pip Reagent

Synonym(s):

N-(2-Aminoethyl)-N-[(tributylstannyl)methyl]-Boc ester

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About This Item

Empirical Formula (Hill Notation):
C20H44N2O2Sn
CAS Number:
1557287-99-6
Molecular Weight:
463.29
UNSPSC Code:
12352103
PubChem Substance ID:
329768680
NACRES:
NA.22

form

liquid

Quality Level

100

refractive index

n/D 1.4860

density

1.108 g/mL

storage temp.

−20°C

SMILES string

CCCC[Sn](CCCC)(CN(C(OC(C)(C)C)=O)CCN)CCCC

InChI

1S/C8H17N2O2.3C4H9.Sn/c1-8(2,3)12-7(11)10(4)6-5-9;3*1-3-4-2;/h4-6,9H2,1-3H3;3*1,3-4H2,2H3;

InChI key

LGYNPAYNCSWDHV-UHFFFAOYSA-N

Related Categories

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 Jeffrey Bode Research Group

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Other Notes

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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Signal Word

Danger

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM9673
MKCJ0885
MKCC2051
MKBZ7778V
MKBZ4436V

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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)

Protocols

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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