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803871

Sigma-Aldrich

Mattson Boronate Urea Pinacol Ester

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About This Item

Formula empirica (notazione di Hill):
C21H21BF6N2O3
Numero CAS:
1538637-10-3
Peso molecolare:
474.20
Numero MDL:
MFCD22570856
Codice UNSPSC:
12352300
ID PubChem:
329768831
NACRES:
NA.22

Saggio

97%

Forma fisica

solid

Impiego in reazioni chimiche

reagent type: catalyst

Caratteristiche più verdi

Catalysis
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Punto di fusione

230.39 °C

Categoria alternativa più verde

, Aligned

Temperatura di conservazione

2-8°C

Stringa SMILE

CC(O1)(C)C(C)(C)OB1C2=CC=CC=C2NC(NC3=CC(C(F)(F)F)=CC(C(F)(F)F)=C3)=O

InChI

1S/C21H21BF6N2O3/c1-18(2)19(3,4)33-22(32-18)15-7-5-6-8-16(15)30-17(31)29-14-10-12(20(23,24)25)9-13(11-14)21(26,27)28/h5-11H,1-4H3,(H2,29,30,31)
OJFYKTGJRXTBRH-UHFFFAOYSA-N

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

1-(3,5-bis(trifluoromethyl)phenyl)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea is a user-friendly, bench stable white solid. When compared to conventional ureas, this urea is moderately acidic (pKa(DMSO) = 9.5) and benefits from improved catalytic abilities and stability in select reactions.

Altre note

Urea Activation of a-Nitrodiazoesters: An Organocatalytic Approach to N–H Insertion Reactions

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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Tyler J Auvil et al.
Angewandte Chemie (International ed. in English), 52(43), 11317-11320 (2013-09-17)
It takes two: A unique organocatalyzed cascade for the unsymmetric double arylation of α-nitrodiazoesters is described. This organocascade features the strategic use of carbene-activating anilines in conjunction with a urea catalyst, thus allowing for the synthesis of pharmaceutically attractive α-diarylesters
Sonia S So et al.
Organic letters, 14(2), 444-447 (2012-01-03)
Boronate ureas operate as catalysts for the activation of nitrocyclopropane carboxylates in nucleophilic ring-opening reactions. A variety of amines were found to open the urea-activated nitrocyclopropane carboxylates, generating highly useful nitro ester building blocks in good yields. Standard manipulations allow
David M Nickerson et al.
Chemical communications (Cambridge, England), 49(39), 4289-4291 (2012-12-01)
The strategic incorporation of internal Lewis acids onto urea scaffolds gives rise to a family of tunable hydrogen bond donor catalysts. The nature of the Lewis acid and associated ligands affects the urea polarization, acidity, and activity in reactions of
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
Andrea M Hardman et al.
Organic & biomolecular chemistry, 11(35), 5793-5797 (2013-08-03)
Highly functionalized oxazinanes are efficiently prepared through urea-catalyzed formal [3 + 3] cycloaddition reactions of nitrones and nitrocyclopropane carboxylates. The reaction system is general with respect to both the nitrocyclopropane carboxylates and nitrones enabling the preparation of a large family
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Contenuto correlato

Anita Mattson – Professor Product Portal

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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