803855

Sigma-Aldrich

Schreiner′s Catalyst

greener alternative
Synonym(s):
N,N′-bis[3,5-bis(trifluoromethyl)phenyl]-Urea, 1,3-Bis[3,5-bis(trifluoromethyl)phenyl]urea
Empirical Formula (Hill Notation):
C17H8F12N2O
CAS Number:
Molecular Weight:
484.24
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

97%

Quality Level

form

powder

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative category

Aligned

storage temp.

2-8°C

SMILES string

O=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/C17H8F12N2O/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

YGCOMBKZFUMALE-UHFFFAOYSA-N

Related Categories

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

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

Packaging

250 mg in glass bottle

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Bonding Organocatalysed Friedel-Crafts Alkylation of Aromatic and Heteroaromatic Systems with Nitroolefins
Dessole G,et al.
Synlett, 13, 2374-2378 (2004)
Sonia S So et al.
Organic letters, 13(4), 716-719 (2011-01-14)
Boronate ureas are introduced as a new class of noncovalent catalysts for conjugate addition reactions with enhanced activity. Through intramolecular coordination of the urea functionality to a strategically placed Lewis acid, rate enhancements up to 10 times that of more...
Sarah A Kavanagh et al.
Organic & biomolecular chemistry, 6(8), 1339-1343 (2008-04-04)
N,N'-Diarylureas have been shown to efficiently catalyse sulfonium ylide-mediated aldehyde epoxidation reactions for the first time. These processes are of broad scope and can be coupled with a subsequent Cu(II) ion-catalysed Meinwald rearrangement to give an efficient and convenient protocol...
Related Content
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.
Read More

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