673862
2-Nitrophenylboronic acid
≥95%
Synonym(s):
o-Nitrobenzeneboronic acid
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About This Item
Linear Formula:
(O2N)C6H4(B(OH)2)
CAS Number:
Molecular Weight:
166.93
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Assay
≥95%
form
powder
mp
155-160 °C
functional group
nitro
SMILES string
OB(O)c1ccccc1[N+]([O-])=O
InChI
1S/C6H6BNO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,9-10H
InChI key
SFUIGUOONHIVLG-UHFFFAOYSA-N
Application
Boronic acid catalyst used for:
Reactant involved in:
- Mild and selective dipolar cycloadditions of unsaturated carboxylic acids with azides
- Transposition of allylic alcohols and Meyer-Schuster rearrangements
Reactant involved in:
- Suzuki-Miyaura cross-coupling reactions with aryl halides or nitroarenediazonium tetrafluoroborates
- Copper-catalyzed halogenation
- Oxidative arylation of aminopyrazolyl disulfides
Used in a preparation of unsymmetrical 2,2′-dinitrobiphenyls via Suzuki-Miyaura cross-coupling with nitrophenyl halides.[1]
Other Notes
May contain varying amounts of anhydride
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
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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Raquel Rodríguez González et al.
The Journal of organic chemistry, 70(23), 9591-9594 (2005-11-05)
[Reaction: see text]. Mechanistic investigations and protocols for the synthesis of 2-nitrobiphenyls and 2,2'-dinitrobiphenyls are disclosed. It is revealed that obstacles appear during the transmetalation step when the phenylboronic acid is substituted with a nitro group in the 2-position, whereas
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