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803871

Sigma-Aldrich

Mattson Boronate Urea Pinacol Ester

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About This Item

Formule empirique (notation de Hill):
C21H21BF6N2O3
Numéro CAS:
1538637-10-3
Poids moléculaire :
474.20
Numéro MDL:
MFCD22570856
Code UNSPSC :
12352300
ID de substance PubChem :
329768831
Nomenclature NACRES :
NA.22

Essai

97%

Forme

solid

Pertinence de la réaction

reagent type: catalyst

Caractéristiques du produit alternatif plus écologique

Catalysis
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Pf

230.39 °C

Autre catégorie plus écologique

, Aligned

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

OJFYKTGJRXTBRH-UHFFFAOYSA-N

Description générale

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Application

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.

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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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
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
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
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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Contenu apparenté

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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