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798894

SnAP DA Reagent

Synonym(s):

tert-Butyl (3-aminopropyl)((tributylstannyl)methyl)carbamate

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About This Item

Empirical Formula (Hill Notation):
C21H46N2O2Sn
CAS Number:
1577233-73-8
Molecular Weight:
477.31
MDL number:
MFCD29037001
UNSPSC Code:
12352103
PubChem Substance ID:
329768679
NACRES:
NA.22
Form:
liquid
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form

liquid

Quality Level

100

functional group

amine, carbamate

storage temp.

−20°C

SMILES string

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

InChI

1S/C9H19N2O2.3C4H9.Sn/c1-9(2,3)13-8(12)11(4)7-5-6-10;3*1-3-4-2;/h4-7,10H2,1-3H3;3*1,3-4H2,2H3;

InChI key

IXXRAKGOXZKYBH-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 require mild reaction conditions and aldehydes bearing aryl, heteroaryl, aliphatic, halogenated and glyoxylates 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

signalword

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

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP2967
MKCM8653

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Protocols

SnAP试剂_饱和N杂环结构单元-默克生命科学

SnAP试剂是一种种类不断扩充的试剂，现在可用来方便地合成中等环（6-9元）饱和N-杂环，包括双环和螺环结构。

SnAP Reagents

SnAP Reagents facilitate synthesis of saturated N-heterocycles for diverse structures.

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
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)
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Global Trade Item Number

SKUGTIN
798894-1G04061826736432
798894-5G04061833341100