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431966

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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$36.50
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$121.00
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$249.46

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1 G
$36.50
5 G
$121.00
25 G
$249.46

About This Item

Linear Formula:
HCOC6H4B(OH)2
CAS Number:
87199-17-5
Molecular Weight:
149.94
Beilstein/REAXYS Number:
3030770
MDL number:
MFCD00151823
UNSPSC Code:
12352103
PubChem Substance ID:
24867058
NACRES:
NA.22

$36.50

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Quality Level

100

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

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Application

4-Formylphenylboronic acid is a substrate for Suzuki cross-coupling reactions[1][2] and it can be used as a reagent for:
  • Palladium-catalyzed Suzuki-Miyaura cross-coupling in water.[3]
  • Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides.[4]
  • Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids.[5]
  • Triethylamine-catalyzed three-component Hantzsch condensations.[6]
  • Copper-catalyzed nitrations.[7]
  • Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta.[8]
  • Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides.[9]
  • Palladium-catalyzed aerobic oxidative cross-coupling reactions.[10]
  • The synthesis of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells.[11]
  • The synthesis of a novel protein synthesis inhibitor active against Gram-positive bacteria.[12]
  • The Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene.[13]
  • 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_germany

WGK 1

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3717
0000344096
0000264421
MKCS7778
0000240905

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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.
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
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)
View All Related Papers

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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