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431966

Sigma-Aldrich

4-Formylphenylboronic acid

≥95.0%

Sinonimo/i:

4-(Dihydroxyboryl)benzaldehyde, 4-Boronobenzaldehyde, 4-Formylbenzeneboronic acid, p-Formylbenzeneboronic acid, p-Formylphenylboronic acid

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About This Item

Formula condensata:
HCOC6H4B(OH)2
Numero CAS:
87199-17-5
Peso molecolare:
149.94
Beilstein:
3030770
Numero MDL:
MFCD00151823
Codice UNSPSC:
12352103
ID PubChem:
24867058
NACRES:
NA.22

Saggio

≥95.0%

Punto di fusione

237-242 °C (lit.)

Gruppo funzionale

aldehyde

Stringa SMILE

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
VXWBQOJISHAKKM-UHFFFAOYSA-N

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Applicazioni

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.

Altre note

Contains varying amounts of anhydride

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H317

Classi di pericolo

Skin Sens. 1

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
MKCN7216
MKCK9984
SHBJ3823
SHBG1441V
SHBD6605V

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Sigma-Aldrich

594539

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4-Cyanophenylboronic acid ≥95%

Sigma-Aldrich

521418

4-Cyanophenylboronic acid

Synthesis of Some New 1,4-Dihydropyridine Derivatives through a Facile One-pot Hantzsch Condensation Catalyzed by Triethylamine
Chin. J. Chem., 30, 733-737 (2012)
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
Tetrahedron, 62, 10321-10321 (2006)
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
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
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