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803863

Sigma-Aldrich

Schreiner′s Thiourea Catalyst

greener alternative

95%

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C17H8F12N2S
CAS-Nummer:
1060-92-0
Molekulargewicht:
500.30
MDL-Nummer:
MFCD00829878
UNSPSC-Code:
12161600
PubChem Substanz-ID:
329768830
NACRES:
NA.22

Qualitätsniveau

100

Assay

95%

Form

powder or crystals

Eignung der Reaktion

reagent type: catalyst

Grünere Alternativprodukt-Eigenschaften

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp (Schmelzpunkt)

170 °C

Grünere Alternativprodukt-Kategorie

Aligned,

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)

InChIKey

RWXWQJYJWJNJNW-UHFFFAOYSA-N

Verwandte Kategorien

Allgemeine Beschreibung

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.

Anwendung

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

Sonstige Hinweise

N,N′-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea: a privileged motif for catalyst development

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H315,H319

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
MKCH2666
MKCD9129

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N,N′-Diphenylthioharnstoff 98%

Sigma-Aldrich

T28355

N,N′-Diphenylthioharnstoff

Stefan H Jungbauer et al.
Chemical communications (Cambridge, England), 50(47), 6281-6284 (2014-05-07)
Using a prototypical Diels-Alder reaction as benchmark, we show that dicationic halogen-bond donors are capable of activating a neutral organic substrate. By various comparison experiments, the action of traces of acid or of other structural features of the halogen-bond donor
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
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)
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
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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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