431966
4-Formylphenylboronic acid
≥95.0%
Synonym(s):
4-(Dihydroxyboryl)benzaldehyde, 4-Boronobenzaldehyde, 4-Formylbenzeneboronic acid, p-Formylbenzeneboronic acid, p-Formylphenylboronic acid
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About This Item
Linear Formula:
HCOC6H4B(OH)2
CAS Number:
Molecular Weight:
149.94
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3030770
Assay:
≥95.0%
Quality Level
assay
≥95.0%
mp
237-242 °C (lit.)
functional group
aldehyde
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
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
signalword
Warning
hcodes
Hazard Classifications
Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 1
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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Related Content
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
Suzuki Coupling at the 2-Position of Densely Functionalized Pyrimidones
Colarusso, Stefania; et al.
Synthesis, 8, 1343-1350 (2006)
Palladacycle-catalyzed cross-coupling reactions of arylboronic acids with carboxylic anhydrides or acyl chlorides
Yu, A.; et al.
Tetrahedron, 68, 2283-2288 (2012)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 431966-1G | 04061832108520 |
| 431966-5G | 04061832108544 |
| 431966-25G | 04061832108537 |