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325104

Sigma-Aldrich

3-Nitrophenylboronic acid

≥97%

Synonym(s):

3-Nitrobenzeneboronic acid, m-Nitrobenzeneboronic acid, m-Nitrophenylboronic acid, NSC 401539, NSC 59739

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About This Item

Linear Formula:
O2NC6H4B(OH)2
CAS Number:
13331-27-6
Molecular Weight:
166.93
Beilstein:
2938638
MDL number:
MFCD00007193
UNSPSC Code:
12352103
PubChem Substance ID:
24859487
NACRES:
NA.22

Quality Level

100

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:
  • 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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