All Photos(3)
Synonym(s):
4-(Dihydroxyboryl)benzaldehyde, 4-Boronobenzaldehyde, 4-Formylbenzeneboronic acid, p-Formylbenzeneboronic acid, p-Formylphenylboronic acid
Linear Formula:
HCOC6H4B(OH)2
CAS Number:
Molecular Weight:
149.94
Beilstein:
3030770
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
≥95.0%
mp
237-242 °C (lit.)
SMILES string
OB(O)c1ccc(C=O)cc1
InChI
1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
InChI key
VXWBQOJISHAKKM-UHFFFAOYSA-N
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Related Categories
Application
4-Formylphenylboronic acid is a substrate for Suzuki cross-coupling reactions and it can be used as a reagent for:
- Palladium-catalyzed Suzuki-Miyaura cross-coupling in water.
- Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides.
- Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids.
- Triethylamine-catalyzed three-component Hantzsch condensations.
- Copper-catalyzed nitrations.
- Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta.
- Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides.
- Palladium-catalyzed aerobic oxidative cross-coupling reactions.
- The synthesis of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells.
- The synthesis of a novel protein synthesis inhibitor active against Gram-positive bacteria.
- The Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene.
- A rhodium-catalyzed cyclization, converting 1,5-enynes to cyclopentenes and spiro-cyclopentenes.
Other Notes
Contains varying amounts of anhydride
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Sens. 1
WGK
WGK 1
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Nora R Eibergen et al.
Chembiochem : a European journal of chemical biology, 13(4), 574-583 (2012-03-01)
In an effort to identify novel antibacterial chemotypes, we performed a whole-cell screen for inhibitors of Staphylococcus aureus growth and pursued those compounds with previously uncharacterized antibacterial activity. This process resulted in the identification of a benzothiazolium salt, ABTZ-1, that
A new and simple synthetic approach to functionalized sulphone derivatives by the Suzuki-Miyaura cross-coupling reaction
Kotha S and Ghosh AK
Indian J. Chem. B, 45(1), 227-231 (2006)
Shi-En Chen et al.
Analytica chimica acta, 1124, 40-51 (2020-06-15)
Glucosylsphingosine (GlcS) in plasma is considered to be a reliable biomarker of Gaucher disease. The detection difficulty of GlcS is that it is difficult to achieve simultaneous separation and quantification with its isomer galactosylsphingosine (GalS), a biomarker of Krabbe disease.
Caroline E Paul et al.
Chemical communications (Cambridge, England), 48(27), 3303-3305 (2012-02-24)
The first report of a biocatalytic regioselective oxidative mono-cleavage of dialkenes was successfully achieved employing a cell-free enzyme preparation from Trametes hirsuta at the expense of molecular oxygen. Selected reactions were performed on a preparative scale affording high to excellent
Palladacycle-catalyzed cross-coupling reactions of arylboronic acids with carboxylic anhydrides or acyl chlorides
Yu, A.; et al.
Tetrahedron, 68, 2283-2288 (2012)
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