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Merck
CN

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:
87199-17-5
Molecular Weight:
149.94
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24867058
MDL number:
MFCD00151823
Beilstein/REAXYS Number:
3030770
Assay:
≥95.0%

Key Documents

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Product Name

4-Formylphenylboronic acid, ≥95.0%

InChI

1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H

SMILES string

OB(O)c1ccc(C=O)cc1

InChI key

VXWBQOJISHAKKM-UHFFFAOYSA-N

assay

≥95.0%

mp

237-242 °C (lit.)

functional group

aldehyde

Quality Level

100

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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

signalword

Warning

hcodes

H317

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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Certificates of Analysis (COA)

Lot/Batch Number
0000489572
0000489572
0000344096
MKCW3717
0000344096

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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
Synthesis of Some New 1,4-Dihydropyridine Derivatives through a Facile One-pot Hantzsch Condensation Catalyzed by Triethylamine
Ghalem W, et al.
Chin. J. Chem., 30, 733-737 (2012)
Suzuki?Miyaura coupling on the three upper rims of hexahomotrioxacalix[3]arenes
Tsubaki K, et al.
Tetrahedron, 62(44), 10321-10321 (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.
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)
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