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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:
3824-74-6
Molecular Weight:
484.24
MDL number:
MFCD00018048
UNSPSC Code:
12161600
PubChem Substance ID:
329768829
NACRES:
NA.22

Assay

97%

form

powder

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
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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

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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.

Other Notes

Acceleration of the DABCO-promoted Baylis–Hillman reaction using a recoverable H-bonding organocatalyst

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM5141
MKCK6548
MKCG1567

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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)
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
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

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