803898

Sigma-Aldrich

Mattson Difluoroborate Urea

greener alternative
Synonym(s):
N-[3,5-bis(trifluoromethyl)phenyl]-N′-[2-(difluoroboryl)phenyl]-Urea
Empirical Formula (Hill Notation):
C15H9BF8N2O
CAS Number:
Molecular Weight:
396.04
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

mp

223-228 °C

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=CC=C2B(F)F

InChI

1S/C15H9BF8N2O/c17-14(18,19)8-5-9(15(20,21)22)7-10(6-8)25-13(27)26-12-4-2-1-3-11(12)16(23)24/h1-7H,(H2,25,26,27)

InChI key

VTRJGINZAJTRDQ-UHFFFAOYSA-N

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

1-(3,5-bis(trifluoromethyl)phenyl)-3-(2-(difluoroboryl)phenyl)urea is a robust and user-friendly white solid capable of being stored on the benchtop indefinitely. The strategic incoporation of the difluoroboryl substituent renders this the most acidic urea catalyst reported to date (pKa(DMSO) = 7.5). This difluorboronate urea benefits from enhanced reaction rates and yields when compared to traditional urea catalysts. It also enables reactions that are inaccessible with conventional urea catalysis.

Packaging

250 mg in glass bottle

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Sonia S So et al.
The Journal of organic chemistry, 79(11), 4832-4842 (2014-05-07)
The power of hydrogen-bond donor catalysis has been harnessed to elicit and control carbene-like reactivity from nitrodiazoesters. Specifically, select ureas have been identified as effective catalysts for N-H insertion and multicomponent coupling reactions of nitrodiazoesters, anilines, and aromatic nucleophiles, thereby...
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...
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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