Skip to Content
MilliporeSigma
All Photos(2)

Documents

798894

Sigma-Aldrich

SnAP DA Reagent

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C21H46N2O2Sn
CAS Number:
Molecular Weight:
477.31
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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.

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

related product

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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 facilitate synthesis of saturated N-heterocycles for diverse structures.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service