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803863

Sigma-Aldrich

Schreiner′s Thiourea Catalyst

greener alternative

95%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C17H8F12N2S
Numero CAS:
1060-92-0
Peso molecolare:
500.30
Numero MDL:
MFCD00829878
Codice UNSPSC:
12161600
ID PubChem:
329768830
NACRES:
NA.22

Livello qualitativo

100

Saggio

95%

Stato

powder or crystals

Impiego in reazioni chimiche

reagent type: catalyst

Caratteristiche più verdi

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

Punto di fusione

170 °C

Categoria alternativa più verde

Aligned,

Stringa SMILE

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)
RWXWQJYJWJNJNW-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

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.

Applicazioni

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

Altre note

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

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
MKCH2666
MKCD9129

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N,N′-Diphenylthiourea 98%

Sigma-Aldrich

T28355

N,N′-Diphenylthiourea

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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