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Merck
CN

798886

SnAP TM Reagent

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About This Item

Empirical Formula (Hill Notation):
C15H35NSSn
CAS Number:
1452829-00-3
Molecular Weight:
380.22
NACRES:
NA.22
PubChem Substance ID:
329768678
UNSPSC Code:
12352103
MDL number:
MFCD23703162

Key Documents

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InChI

1S/3C4H9.C3H8NS.Sn/c3*1-3-4-2;1-5-3-2-4;/h3*1,3-4H2,2H3;1-4H2;

SMILES string

CCCC[Sn](CCCC)(CSCCN)CCCC

InChI key

DYBMHPJDHUKXRF-UHFFFAOYSA-N

form

liquid

refractive index

n/D 1.512

density

1.158 at 25 °C

functional group

amine
thioether

storage temp.

−20°C

Quality Level

100

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 Bode Research Group
SnAP TM Reagent may be used to synthesize 3-substituted thiomorpholines from aldehydes. It may also be used in the preparation of unprotected, saturated N-heterocyclic compounds.

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

General description

SnAP (Sn amino protocol) reagents have been developed by the Bode group. SnAP reagents are air and moisture stable. They can be prepared from simple reactions with cheap raw materials. SnAP 2-Spiro-(4-Pip) M, also referred to as SnAP 2-spiro-(4-piperdine) morpholine, is a regioisomeric SnAP reagent. This reagent can be prepared from N-Boc piperidone.

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
Bespoke SnAP Reagents for the Synthesis of C-Substituted Spirocyclic and Bicyclic 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
MKBX2274V
MKBZ4437V

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SnAP Reagents for a Cross-Coupling Approach to the One-Step Synthesis of Saturated N-Heterocycles.
Luescher MU, et al.
Aldrichimica Acta, 48(2), 43-48 (2015)
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

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

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。

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