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803855

Sigma-Aldrich

Schreiner′s Catalyst

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Synonym(s):

1,3-Bis[3,5-bis(trifluoromethyl)phenyl]urea, N,N′-bis[3,5-bis(trifluoromethyl)phenyl]-Urea

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About This Item

Empirical Formula (Hill Notation):
C17H8F12N2O
CAS Number:
Molecular Weight:
484.24
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

powder

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
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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

General description

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Application

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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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.

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