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Merck

803863

Sigma-Aldrich

Schreiner′s Thiourea Catalyst

greener alternative

95%

Sinónimos:

N,N′−bis[3,5−bis(trifluoromethyl)phenyl]−Thiourea

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About This Item

Fórmula empírica (notación de Hill):
C17H8F12N2S
Número de CAS:
Peso molecular:
500.30
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

form

powder or crystals

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

170 °C

greener alternative category

SMILES string

S=C(NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)NC2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2

InChI

1S/C17H8F12N2S/c18-14(19,20)7-1-8(15(21,22)23)4-11(3-7)30-13(32)31-12-5-9(16(24,25)26)2-10(6-12)17(27,28)29/h1-6H,(H2,30,31,32)

InChI key

RWXWQJYJWJNJNW-UHFFFAOYSA-N

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

Thiourea catalyst, also known as Schreiner′s Thiourea, is commonly used as a hydrogen-bond donor in the activation of carbonyls, nitroolefins, imines etc.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Water-compatible hydrogen-bond activation: a scalable and organocatalytic model for the stereoselective multicomponent aza-Henry reaction.
Fabio Cruz-Acosta et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(49), 16550-16554 (2013-11-28)
Michael T Corbett et al.
Organic letters, 16(9), 2362-2365 (2014-04-22)
The stereoselective synthesis of trisubstituted 2-trifluoromethyl pyrrolidines by asymmetric Michael addition/hydrogenative cyclization is described. The direct organocatalytic addition of 1,1,1-trifluoromethylketones to nitroolefins proceeds under mild reaction conditions and low catalyst loadings to provide Michael adducts in high yield with excellent
Thiophosphoramide-based cooperative catalysts for Brønsted acid promoted ionic Diels-Alder reactions.
Alina Borovika et al.
Angewandte Chemie (International ed. in English), 52(50), 13424-13428 (2013-10-19)
Peter R Schreiner et al.
Organic letters, 4(2), 217-220 (2002-02-14)
[reaction: see text] A combination of NMR, IR, and ab initio techniques reveals the striking structural similarities of an exemplary H-bonded complex of an N-acyloxazolidinone with an N,N'-disubstituted electron-poor thiourea and the corresponding Lewis acid complex. Although the H-bond association
Alexander Wittkopp et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 9(2), 407-414 (2003-01-18)
We examined the catalytic activity of substituted thioureas in a series of Diels-Alder reactions and 1,3-dipolar cycloadditions. The kinetic data reveal that the observed accelerations in the relative rates are more dependent on the thiourea substituents than on the reactants

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Boronate ureas benefit from internal Lewis acid coordination of the urea cabonyl oxygen and the strategically placed boron. As a result of this structural feature, boronate ureas can be rendered more acidic than conventional urea hydrogen bond donor catalysts.

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