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190788-59-1 molecular structure
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(2-nitrophenyl)boronic acid

ChemBase ID: 74809
Molecular Formular: C6H6BNO4
Molecular Mass: 166.92714
Monoisotopic Mass: 167.03898808
SMILES and InChIs

SMILES:
B(c1ccccc1[N+](=O)[O-])(O)O
Canonical SMILES:
[O-][N+](=O)c1ccccc1B(O)O
InChI:
InChI=1S/C6H6BNO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,9-10H
InChIKey:
SFUIGUOONHIVLG-UHFFFAOYSA-N

Cite this record

CBID:74809 http://www.chembase.cn/molecule-74809.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2-nitrophenyl)boronic acid
IUPAC Traditional name
2-nitrophenylboronic acid
Synonyms
2-Nitrobenzeneboronic acid
o-Nitrobenzeneboronic acid
2-Nitrophenylboronic acid
2-Nitrophenylboronic acid
2-Nitrobenzeneboronic acid
(2-Nitrophenyl)boronic acid
2-Nitrophenylboronic acid
2-硝基苯硼酸
CAS Number
190788-59-1
5570-19-4
MDL Number
MFCD00161358
Beilstein Number
3032097
PubChem SID
24885182
162039727
PubChem CID
2773548

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Rotatable Bonds Lipinski's Rule of Five true 
Acid pKa 7.8239956  H Acceptors
H Donor LogD (pH = 5.5) 1.5913564 
LogD (pH = 7.4) 1.4550395  Log P 1.5934 
Molar Refractivity 36.924 cm3 Polarizability 15.469442 Å3
Polar Surface Area 83.6 Å2

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
149-151°C expand Show data source
155-160 °C expand Show data source
Storage Warning
Harmful expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
36/37/38 expand Show data source
Safety Statements
26 expand Show data source
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319-H335 expand Show data source
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
96% expand Show data source
97% expand Show data source
98% expand Show data source
Linear Formula
(O2N)C6H4(B(OH)2) expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 673862 external link
Application
Used in a preparation of unsymmetrical 2,2′-dinitrobiphenyls via Suzuki-Miyaura cross-coupling with nitrophenyl halides.7
Boronic acid catalyst used for:
• Mild and selective dipolar cycloadditions of unsaturated carboxylic acids with azides1
• Transposition of allylic alcohols and Meyer-Schuster rearrangements2Reactant involved in:
• Suzuki-Miyaura cross-coupling reactions with aryl halides3 or nitroarenediazonium tetrafluoroborates4
• Copper-catalyzed halogenation5
• Oxidative arylation of aminopyrazolyl disulfides6
Other Notes
May contain varying amounts of anhydride
Packaging
1, 5 g in glass bottle

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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