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803863

Sigma-Aldrich

Schreiner′s Thiourea Catalyst

greener alternative

95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C17H8F12N2S
CAS Number:
Molecular Weight:
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.

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Greener Alternative Product

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170 °C

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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.

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Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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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
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
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
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)
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)

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