325104
3-Nitrophenylboronic acid
≥97%
Synonym(s):
3-Nitrobenzeneboronic acid, m-Nitrobenzeneboronic acid, m-Nitrophenylboronic acid, NSC 401539, NSC 59739
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All Photos(3)
About This Item
Linear Formula:
O2NC6H4B(OH)2
CAS Number:
Molecular Weight:
166.93
Beilstein:
2938638
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
≥97%
form
powder
mp
284-285 °C (dec.) (lit.)
SMILES string
OB(O)c1cccc(c1)[N+]([O-])=O
InChI
1S/C6H6BNO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,9-10H
InChI key
ZNRGSYUVFVNSAW-UHFFFAOYSA-N
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Application
Reactant involved in:
Additionally used as a reactant for synthesizing biologically active molecules such as:
- Copper-catalyzed arylation
- Palladium-catalyzed decarboxylative coupling
- Suzuki-Miyaura cross-coupling
- Oxidative carbocyclization / arylation
- Addition to arylpropargyl alcohols
Additionally used as a reactant for synthesizing biologically active molecules such as:
- Inhibitors of angiogenesis
- Biaryl-olefins with antiproliferative activities
Catalyzes ene carbocyclization of acetylenic dicarbonyl compounds
Other Notes
Contains varying amounts of anhydride
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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The discovery and development of an efficient ene carbocyclization of 1,3-dicarbonyl compounds bearing pendent terminal alkyne substituents under 3-nitrobenzeneboronic acid catalysis is described. The reaction is efficient, easy to perform and general to a wide range of ketoester substrates.
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Inorganic chemistry, 47(5), 1417-1419 (2008-02-12)
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