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Sigma-Aldrich

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:
87199-17-5
Molecular Weight:
149.94
Beilstein:
3030770
MDL number:
MFCD00151823
UNSPSC Code:
12352103
PubChem Substance ID:
24867058
NACRES:
NA.22

Quality Level

100

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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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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Ghazale Gholami et al.
Faraday discussions, 225, 358-370 (2020-10-23)
Zr(iv) metal-organic frameworks (MOFs) UiO-68 and PCN-57, containing triphenylene dicarboxylate (TPDC) and tetramethyl-triphenylene dicarboxylate (TTDC) linkers, respectively, were doped with an H-shaped tetracarboxylate linker that contains a [2]rotaxane molecular shuttle. The new MOFs, UWDM-8 and UWDM-9, contain a [2]rotaxane crossbar
Qi Huang et al.
ACS applied materials & interfaces, 11(17), 15861-15868 (2019-03-28)
Conjugated microporous polymers (CMPs) with high surface areas, tunable building blocks, and fully conjugated structures have found important applications in optoelectronics. Here, we report a new series of CMPs with tunable band gaps by introducing thiazolo[5,4- d] thiazole as the
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)
Suzuki?Miyaura coupling on the three upper rims of hexahomotrioxacalix[3]arenes
Tsubaki K, et al.
Tetrahedron, 62(44), 10321-10321 (2006)
Kunpeng Guo et al.
Organic letters, 14(9), 2214-2217 (2012-04-14)
This work identifies the dithiafulvenyl unit as an excellent electron donor for constructing D-π-A-type metal-free organic sensitizers of dye-sensitized solar cells (DSCs). Synthesized and tested are three sensitizers all with this donor and a cyanoacrylic acid acceptor but differing in
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