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Documenti fondamentali

523976

Sigma-Aldrich

4-Hydroxyphenylboronic acid

≥95.0%

Sinonimo/i:

(p-Hydroxyphenyl)boronic acid, 4-Hydroxybenzeneboronic acid, p-hydroxy-benzeneboronic acid

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About This Item

Formula condensata:
HOC6H4B(OH)2
Numero CAS:
Peso molecolare:
137.93
Numero MDL:
Codice UNSPSC:
12352103
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

≥95.0%

Stato

solid

Punto di fusione

>230 °C (lit.)

Stringa SMILE

OB(O)c1ccc(O)cc1

InChI

1S/C6H7BO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8-10H
COIQUVGFTILYGA-UHFFFAOYSA-N

Applicazioni

4-Hydroxyphenylboronic acid can be used as a reactant in:
  • Suzuki-Miyaura coupling and Stille coupling reactions.
  • Palladium-catalyzed aminocarbonylation and cross-coupling reactions.
  • Suzuki reaction for preparation of bio-supported palladium nanoparticles as phosphine-free catalysts.
  • Cu2O-catalyzed aerobic oxidative cross-coupling of tetrazoles.

It can also be used to prepare/promote:
  • PDK1 inhibitory activity (cancer cell growth, survival, and tumorigenesis inhibitor).
  • Rod-like dendronized polymers containing G4 and G5 ester dendrons via macromonomer approach by living ROMP.
  • Estrone-derived cyclopamine analogs as Sonic Hedgehog signaling inhibitors for anti-cancer chemotherapeutics.
  • Enzymatic inhibitors for the treatment of Gram-negative bacterial infections.
  • Oligoarenes by Suzuki-Miyaura palladium-catalyzed cross-coupling.

Altre note

Contains varying amounts of anhydride

Pittogrammi

Exclamation mark

Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


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Zhaoyang Lu et al.
Soft matter, 12(17), 3860-3867 (2016-03-31)
The self-assembling behavior of coil-rod-coil molecules 1a, 1b, and 2a, 2b was investigated using DSC, POM, SAXS, and AFM in bulk and aqueous solutions. These molecules contain p-quinquephenyl groups as rod segments incorporating lateral hydroxyl or methoxyl groups in the
Stéphanie Blanchard et al.
Bioorganic & medicinal chemistry letters, 22(8), 2880-2884 (2012-03-23)
A series of 2-anilino substituted 4-aryl-8H-purines were prepared as potent inhibitors of PDK1, a serine-threonine kinase thought to play a role in the PI3K/Akt signaling pathway, a key mediator of cancer cell growth, survival and tumorigenesis. The synthesis, SAR and
Synthetic approach to the chemical isostere of O-methyl honokiol
Cui, M.; Kim, H. S.
Synlett, 23, 311-313 (2012)
Highly selective palladium-catalyzed aminocarbonylation and cross-coupling reactions on a cavitand scaffold
Csok, Z.; Takatsy, A.; Kollar, L.
Tetrahedron, 68, 2657-2661 (2012)
Synthesis of Rod-Like Dendronized Polymers Containing G4 and G5 Ester Dendrons via Macromonomer Approach by Living ROMP
Kim, K.O.; Choi, T-L.
ACS Macro Letters, 1, 445-448 (2012)

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