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Merck
CN

803898

Mattson Difluoroborate Urea

greener alternative

Synonym(s):

N-[3,5-bis(trifluoromethyl)phenyl]-N′-[2-(difluoroboryl)phenyl]-Urea

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About This Item

Empirical Formula (Hill Notation):
C15H9BF8N2O
CAS Number:
1451048-80-8
Molecular Weight:
396.04
UNSPSC Code:
12352300
PubChem Substance ID:
329768832
NACRES:
NA.22

Key Documents

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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

form

powder

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
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mp

223-228 °C

greener alternative category

Aligned,

storage temp.

2-8°C

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.

General description

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Other Notes

Arylation of Diazoesters by a Transient N-H Insertion Organocascade

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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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

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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